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

HRID 368374Notes

Reaction equation

HRID 368374 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 14-scheme 12 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 10 with a strong base like NaOH in a protic solvent (i.e., EtOH).

Sources & evidence

ORD record
ord-7790a7772dc343f882de697649dadc6f
Source dataset
uspto-grants-2000_10
Patent number
US06133319

Reaction notes

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