(4-Methoxy-7-nitro-benzothiazol-2-yl)-carbamic acid methyl ester → (7-Amino-4-methoxy-benzothiazol-2-yl)-carbamic acid methyl ester

HRID 51857Notes

Reaction equation

HRID 51857 reaction equation
[CH3:1][O:2][C:3](=[O:19])[NH:4][C:5]1[S:6][C:7]2[C:13]([N+:14]([O-])=O)=[CH:12][CH:11]=[C:10]([O:17][CH3:18])[C:8]=2[N:9]=1>CO.ClCCl.[Pt](=O)=O>[CH3:1][O:2][C:3](=[O:19])[NH:4][C:5]1[S:6][C:7]2[C:13]([NH2:14])=[CH:12][CH:11]=[C:10]([O:17][CH3:18])[C:8]=2[N:9]=1

Participants

5

Reactant 1

HCID 21303402(4-Methoxy-7-nitro-benzothiazol-2-yl)-carbamic acid methyl ester

Product 1

HCID 21303404(7-Amino-4-methoxy-benzothiazol-2-yl)-carbamic acid methyl esterYield 90%

Reagents, catalysts & solvents 3

HCID 345198Adams' catalystCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 5.00 g (17.7 mmol) (4-methoxy-7-nitro-benzothiazol-2-yl)-carbamic acid methyl ester in 140 ml methanol and 140 ml dichloromethane was added 1.5 g platinum (IV) oxide and the mixture was then stirred for 16 hours at room temperature under an atmosphere of hydrogen. The mixture was then filtered and the filtrate concentrated in vacuo to afford 4.03 g (90%) (7-amino-4-methoxy-benzothiazol-2-yl)-carbamic acid methyl ester as a grey crystalline solid. ES-MS m/e (%):276 (M+Na+, 28), 254 (M+H+, 100).

Workup

  1. filtrationThe mixture was then filtered
  2. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-45257b2d06384d74bc256385de5ba564
Source dataset
uspto-grants-2004_03
Patent number
US06713499B2

Reaction notes

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