2-Aminothiophenol → Benzo(d)thiazol-2-amine

HRID 368373Notes

Reaction equation

HRID 368373 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[SH:8].[C:9]1([NH:15]C2C=CC=CC=2)C=CC=CC=1.[S-]C#N.BrBr>>[NH2:15][C:9]1[S:8][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[N:1]=1

Participants

5

Reactant 4

HCID 87132-AminothiophenolHCID 9322ThiocyanateHCID 11487DiphenylamineHCID 24408Bromine

Product 1

HCID 8706Benzo(d)thiazol-2-amine

Procedure

If the desired 2-amino benzenethiol 11-scheme 5 is not commercially available it can be synthesized by reaction of the phenyl aniline with the thiocyanate anion in the presence of an oxidant (like bromine) to produce the 2-amino benzthiazole. This thiazole can then be hydrolyzed to the desired 2-amino benzenethiol 12-scheme 5 with a strong base like NaOH in a protic solvent (i.e., EtOH).

Sources & evidence

ORD record
ord-8b926ef3186741aa85b3869c3a3011e8
Source dataset
uspto-grants-2000_10
Patent number
US06133319

Reaction notes

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