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

HRID 612620Notes

Reaction equation

HRID 612620 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 8-scheme 3 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 7-scheme 3. This thiazole can then be hydrolyzed to the desired 2-amino benzenethiol 8-scheme 3 with a strong base like NaOH in a protic solvent (i.e., EtOH). ##STR11##

Sources & evidence

ORD record
ord-9f6e247f1d374c8380a854a43cb9b4f7
Source dataset
uspto-grants-1999_12
Patent number
US06005008

Reaction notes

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