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

HRID 1956613Notes

Reaction equation

HRID 1956613 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). ##STR15## a) TBSCl, imid, DMF b)i) ClCXCl, NaHCO3, ii) PhNH2 c) Et3 N.HF, CH3CN

Sources & evidence

ORD record
ord-e7527ab664664a6ebac4d90886aa86f3
Source dataset
uspto-grants-1998_07
Patent number
US05780483

Reaction notes

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