2-Nitrophenol → 1,3-benzoxazole-2-thiol

HRID 512438Notes

Reaction equation

HRID 512438 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[OH:10])([O-])=O.O(CC)[C:12]([S-])=[S:13].[K+]>>[SH:13][C:12]1[O:10][C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:1]=1

Participants

3

Reactant 2

HCID 69472-Nitrophenol2×HCID 2735045Potassium ethylxanthate

Product 1

HCID 1784182821,3-benzoxazole-2-thiol

Procedure

In Scheme 3, substituted phenol E can be nitrated to give the corresponding ortho-nitrophenol F. This material can then be reduced to provide the ortho-aminophenol G. The aminophenol G can subsequently be reacted with potassium ethyl xanthate (potassium (carbodithiolatooxy)ethane) to produce the cyclized 2-mercaptobenzoxazole H. Reaction of the 2-mercaptobenzoxazole H with a chlorinating agent, such as thionyl chloride, affords the desired 2-chlorobenzoxazole J.

Sources & evidence

ORD record
ord-0a264c2121b943a28d3012c8378dec48
Source dataset
uspto-grants-2015_08
Patent number
US09102636B2

Reaction notes

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