3-Bromophenyl Isothiocyanate → 2-amino-4-bromobenzene-1-thiol

Reaction equation

BrC1C=C(N=C=S)C=CC=1.BrC1C=C(NC(N)=S)C=CC=1.NC1[S:24][C:25]2[CH:31]=[CH:30][C:29]([Br:32])=[CH:28][C:26]=2[N:27]=1>>[NH2:27][C:26]1[CH:28]=[C:29]([Br:32])[CH:30]=[CH:31][C:25]=1[SH:24]

Participants

Reactant 3

HCID 164813-Bromophenyl Isothiocyanate

HCID 2735619(3-Bromophenyl)thiourea

HCID 137757855-Bromo-1,3-benzothiazol-2-amine

Product 1

HCID 121992942-amino-4-bromobenzene-1-thiolYield 21.1%

Procedure

The procedure of Referential Example 16 was repeated, except that 3-bromophenyl isothiocyanate (25.0 g) serving as a starting material was used, to thereby yield N-(3-bromophenyl)thiourea (19.4 g) as colorless crystals. Subsequently, The procedure of Referential Example 17 was repeated, to thereby yield 2-amino-5-bromobenzothiazole (1.21 g). Thereafter, The procedure of Referential Example 18 was repeated, to thereby yield the title compound (227 mg).

Sources & evidence

ORD record: ord-ca815ff4795c42b7a281b92c22f6ffe2
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08022075B2

Reaction notes

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