Water → 2-Amino-2-(2,3-dichlorophenyl)ethyl carbamate
Reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH:9]([NH:12]C(=O)OC(C)(C)C)[CH2:10][OH:11].ClS([N:24]=[C:25]=[O:26])(=O)=O.O.C(=O)([O-])O.[Na+]>C(#N)C>[C:25](=[O:26])([O:11][CH2:10][CH:9]([NH2:12])[C:3]1[CH:4]=[CH:5][CH:6]=[C:7]([Cl:8])[C:2]=1[Cl:1])[NH2:24]Participants
6
Conditions
- Temperature
- 60 °C
Procedure
Of the compound from Example 182A, 290 mg (about 0.95 mmol) were introduced in 5 ml of acetonitrile under argon. At −15° C., 115 μl (1.33 mmol) of chlorosulphonyl isocyanate were added dropwise. After 30 min, the reaction solution was admixed with 20 ml of water and heated at 60° C. overnight. The reaction mixture was cooled and introduced into saturated aqueous sodium hydrogen carbonate solution. It was extracted with twice 20 ml of ethyl acetate. The combined organic phases were dried over sodium sulphate, filtered and freed from the solvent on a rotary evaporator. Drying in an HV gave 176 mg (66% of theory) of the title compound in 89% purity.
Workup
- temperatureThe reaction mixture was cooled
- extractionIt was extracted with twice 20 ml of ethyl acetate
- dry with materialThe combined organic phases were dried over sodium sulphate
- filtrationfiltered
- customfreed from the solvent on a rotary evaporator
- customDrying in an HV
Sources & evidence
- ORD record
- ord-f52834b62de54de6ab4ceb3680d844b1
- Source dataset
- uspto-grants-2012_06
- Patent number
- US08202895B2
Reaction notes
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