Potassium Hydroxide → 2-Amino-5-methoxybenzene-1-thiol

HRID 609551Notes

Reaction equation

HRID 609551 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+]>C(O)(=O)C>[NH2:6][C:5]1[CH:7]=[CH:8][C:9]([O:11][CH3:12])=[CH:10][C:4]=1[SH:3]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 156302-Amino-6-methoxybenzothiazole

Product 1

HCID 2355092-Amino-5-methoxybenzene-1-thiolYield 81%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 2-amino-6-methoxybenzothiazole (36 g, 200 mmol; Aldrich Chemical Co.) and 400 ml 30% aqueous potassium hydroxide was refluxed for 16 h. The dark solution was cooled to 0° C. and neutralized to pH 6 with 50% aqueous acetic acid and stirred for 1 h. The resulting slurry was filtered and the product collected on the filter paper and dried (25.29 g, 81% yield). 1H NMR (DMSO-d6) δ 6.91-6.44 (m, 3H), 5.90 (br s, 2H). 3.52 (s, 3H). MS Da/e=154 (M-H).

Workup

  1. filtrationThe resulting slurry was filtered
  2. customthe product collected on the filter paper
  3. customdried (25.29 g, 81% yield)

Sources & evidence

ORD record
ord-afad695efa244848983107e8e347b6bc
Source dataset
uspto-grants-1999_12
Patent number
US05998400

Reaction notes

Loading…