Formic Acid → N-tert.-butyl-2-dimethylaminocarbonyl-5-formylaminobenzenesulfonamide
Reaction equation
[CH:1](O)=[O:2].C(OC(=O)C)(=O)C.[NH2:11][C:12]1[CH:13]=[CH:14][C:15]([C:26]([N:28]([CH3:30])[CH3:29])=[O:27])=[C:16]([S:18]([NH:21][C:22]([CH3:25])([CH3:24])[CH3:23])(=[O:20])=[O:19])[CH:17]=1.CN(C)C=O>C(OCC)(=O)C>[C:22]([NH:21][S:18]([C:16]1[CH:17]=[C:12]([NH:11][CH:1]=[O:2])[CH:13]=[CH:14][C:15]=1[C:26]([N:28]([CH3:30])[CH3:29])=[O:27])(=[O:19])=[O:20])([CH3:25])([CH3:24])[CH3:23]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
A mixture of 0.34 ml of formic acid and 0.70 ml of acetic anhydride is heated at 50° C. for 2 hours, and a solution of 0.85 g of 5-amino-N-tert.-butyl-2-dimethylaminocarbonyl-benzenesulfonamide (Example e) and 3.5 ml of dimethylformamide (DMF) is added. After 4 hours, the mixture is taken up in ethyl acetate and washed successively with dilute hydrochloric acid and saturated NaHCO3 solution. After the mixture has been dried over MgSO4 and the organic phase has been concentrated, 0.88 g of a highly viscous substance, which is used in subsequent reactions without further purification (Example j), is obtained.
Workup
- washwashed successively with dilute hydrochloric acid and saturated NaHCO3 solution
- dry with materialAfter the mixture has been dried over MgSO4
- concentrationthe organic phase has been concentrated
- custom0.88 g of a highly viscous substance, which is used in subsequent reactions without further purification (Example j)
- customis obtained
Sources & evidence
- ORD record
- ord-2f2d58adfdf947618250318f4f46afef
- Source dataset
- uspto-grants-2002_12
- Patent number
- US06498253B1
Reaction notes
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