2-Amino-6-methoxybenzothiazole → 2-Amino-5-methoxybenzene-1-thiol

HRID 974814Notes

Reaction equation

HRID 974814 reaction equation
NC1[S:3][C:4]2[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:5]=2[N:6]=1>[OH-].[K+]>[NH2:6][C:5]1[CH:7]=[CH:8][C:9]([O:11][CH3:12])=[CH:10][C:4]=1[SH:3]

Participants

3

Reactant 1

HCID 156302-Amino-6-methoxybenzothiazole

Product 1

HCID 2355092-Amino-5-methoxybenzene-1-thiol

Reagents, catalysts & solvents 1

HCID 14797Potassium HydroxideSolvent

Procedure

To 2-amino-6-methoxy-1,3-benzthiazole (5 g, 0.027M) was added to a solution of potassium hydroxide (25 g in 50 ml of water). The mixture was heated at 140° for 5 hours. The crude 2-amino-5-methoxybenzenethiol produced was diluted with water (150 ml) and to this was added copper powder (1.25 g, 1 equivalent) and iodobenzoic acid (6.8 g, 1 equivalent). The mixture was heated under reflux for 4 hours under nitrogen. On cooling the mixture was filtered to remove copper, and acidified with concentrated hydrochloric acid. The solution was filtered to give the product as a light green solid (5 g).

Workup

  1. temperatureThe mixture was heated at 140° for 5 hours

Sources & evidence

ORD record
ord-8c3042bdd0264aec9919485ebc639a17
Source dataset
uspto-grants-1997_03
Patent number
US05607929

Reaction notes

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