2-Amino-1,3-benzothiazol-5-ol → 3-Methoxyaniline

HRID 1091280Notes

Reaction equation

HRID 1091280 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][C:5]=2[N:6]=1.[NH2:12][C:13]1SC2C(O)=CC=CC=2N=1>>[CH3:13][O:11][C:8]1[CH:7]=[C:5]([CH:4]=[CH:10][CH:9]=1)[NH2:6].[S-:3][C:2]#[N:1].[NH4+:12]

Participants

4

Reactant 2

HCID 141950132-Amino-1,3-benzothiazol-5-olHCID 450774597-Benzothiazolol,2-amino-(9CI)

Product 2

HCID 108243-MethoxyanilineHCID 15666Ammonium thiocyanate

Procedure

The two derivatives that are not commercially available (2-amino-benzothiazol-5-ol and 2-amino-benzothiazol-7-ol) can be obtained by cyclization of 3-methoxyaniline with ammoniumthiocyanate followed by demethylation with boron tribromide as outlined in the scheme below:

Sources & evidence

ORD record
ord-0eb7448356d8486296e793d9e104e226
Source dataset
uspto-grants-2012_03
Patent number
US08129374B2

Reaction notes

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