Highly chemoselective acylation of substituted aminophenols with 3-(trimethylacetyl)-1,3-thiazolidine-2-thione was written by Dai, Wei-Min;Cheung, Yuk King;Tang, Kit Wan;Choi, Pui Yiu;Chung, Suet Lam. And the article was included in Tetrahedron in 1995.Recommanded Product: 56619-93-3 This article mentions the following:
A general procedure for chemoselective acylation of substituted aminophenols has been developed. The N-acylated products were prepared in 70-100% yield by treating the aminophenols with 3-(trimethylacetyl)-1,3-thiazolidine-2-thione (1) in refluxing THF. The pivalate esters of 3- and 4-aminophenols could be obtained in 70-94% yield by treating with 1 and NaH. In the experiment, the researchers used many compounds, for example, N-(3-Methoxyphenyl)pivalamide (cas: 56619-93-3Recommanded Product: 56619-93-3).
N-(3-Methoxyphenyl)pivalamide (cas: 56619-93-3) belongs to ethers. Ether is less polar than esters, alcohols or amines because of the oxygen atom that is unable to participate in hydrogen bonding due to the presence of bulky alkyl groups on both sides of the oxygen atom. Ethers are good solvents partly because they are not very reactive. Most ethers can be cleaved, however, by hydrobromic acid (HBr) to give alkyl bromides or by hydroiodic acid (HI) to give alkyl iodides.Recommanded Product: 56619-93-3
Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem