Dicyclohexylcarbodiimide → 2,6-Dichlorophenyl N-[(4,6-dimethoxypyridin-2-yl)carbonyl]sulfamate

HRID 2081915Notes

Reaction equation

HRID 2081915 reaction equation
[S:1](=[O:13])(=[O:12])([O:3][C:4]1[C:9]([Cl:10])=[CH:8][CH:7]=[CH:6][C:5]=1[Cl:11])[NH2:2].[CH:14]1(N=C=NC2CCCCC2)CCCCC1.[CH3:29][O:30][C:31]1[CH:36]=[C:35]([O:37][CH3:38])N=[C:33]([C:39]([OH:41])=O)[N:32]=1>CN(C)C1C=CN=CC=1.ClCCl>[CH3:38][O:37][C:35]1[CH:36]=[C:31]([O:30][CH3:29])[N:32]=[C:33]([C:39]([NH:2][S:1](=[O:13])(=[O:12])[O:3][C:4]2[C:5]([Cl:11])=[CH:6][CH:7]=[CH:8][C:9]=2[Cl:10])=[O:41])[CH:14]=1

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 44224834,6-Dimethoxypyrimidine-2-carboxylic acidHCID 190184672,6-Dichlorophenyl sulfamate

Product 1

HCID 197788912,6-Dichlorophenyl N-[(4,6-dimethoxypyridin-2-yl)carbonyl]sulfamate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

2.4 g of 2,6-dichlorophenyl sulfamate are added in portions at 0° C. to 2° C. to a mixture of 2.3 g of dicyclohexylcarbodiimide, 120 mg of 4-dimethylaminopyridine and 2.2 g of 4,6-dimethoxypyrimidine-2-carboxylic acid in 80 ml of absolute dichloromethane, and stirring is continued for 0.5 hour at 0° C. and 3 hours at room temperature. The mixture is filtered off with suction, the organic phase is washed with 100 ml of 1N hydrochloric acid and then with water and dried over sodium sulfate. The solvent is distilled off, and the residue is recrystallized from diisopropyl ether. This gives 3.2 g of 2,6-dichlorophenyl N-[(4,6-dimethoxypyrimidin-2-yl)carbonyl]sulfamate of melting point 136°-139° C.

Workup

  1. filtrationThe mixture is filtered off with suction
  2. washthe organic phase is washed with 100 ml of 1N hydrochloric acid
  3. dry with materialwith water and dried over sodium sulfate
  4. distillationThe solvent is distilled off
  5. customthe residue is recrystallized from diisopropyl ether

Sources & evidence

ORD record
ord-8e67242de7e444d7b01492a4719f2264
Source dataset
uspto-grants-1993_02
Patent number
US05186736

Reaction notes

Loading…