Dicyclohexylcarbodiimide → HCID 19018489, compound

HRID 1109982Notes

Reaction equation

HRID 1109982 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:13]=[CH:12][CH:11]=[CH:10][C:4]=1[CH2:5][S:6]([NH2:9])(=[O:8])=[O:7].C1(N=C=NC2CCCCC2)CCCCC1.[CH3:31][O:32][C:33]1[N:38]=[C:37]([CH3:39])[N:36]=[C:35]([C:40](O)=[O:41])[CH:34]=1>CN(C)C1C=CN=CC=1.ClCCl>[F:15][C:2]([F:14])([F:1])[C:3]1[CH:13]=[CH:12][CH:11]=[CH:10][C:4]=1[CH2:5][S:6]([NH:9][C:40]([C:35]1[CH:34]=[C:33]([O:32][CH3:31])[N:38]=[C:37]([CH3:39])[N:36]=1)=[O:41])(=[O:7])=[O:8]

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 142756951-[2-(Trifluoromethyl)phenyl]methanesulfonamideHCID 19018484HCID 19018484, compound

Product 1

HCID 19018489HCID 19018489, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

2.4 g of 2-trifluoromethylbenzylsulfonamide are added in portions at 0°-2° C. to a mixture of 2.3 g of dicyclohexylcarbodiimide, 120 mg of 4-dimethylaminopyridine and 2.0 g of 6-methoxy-2-methylpyrimidine-4-carboxylic acid in 80 ml of abs. dichloromethane. The mixture is then stirred at 0° C. for 1/2 h, allowed to warm to room temperature and then stirred for 14 h. The precipitated urea is filtered off with suction, the solvent is distilled off under reduced pressure, and the residue is dissolved in acetone and stirred with 100 ml of 1N aqueous sodium carbonate solution for 1/2 h. The solid is filtered off, the filtrate is extracted with diethyl ether and acidified with conc. hydrochloric acid, and the product is filtered off with suction and dried at 50° C./20 mbar [lacuna] 2-Trifluoromethyl-N-[(6-methoxy-2-methylpyrimidin-4-yl)carbonyl]benzylsulfonamide of melting point 120°-122° C. is obtained in this way.

Workup

  1. temperatureto warm to room temperature
  2. stirringstirred for 14 h
  3. filtrationThe precipitated urea is filtered off with suction
  4. distillationthe solvent is distilled off under reduced pressure
  5. dissolutionthe residue is dissolved in acetone
  6. stirringstirred with 100 ml of 1N aqueous sodium carbonate solution for 1/2 h
  7. filtrationThe solid is filtered off
  8. extractionthe filtrate is extracted with diethyl ether
  9. filtrationthe product is filtered off with suction
  10. dry with materialdried at 50° C./20 mbar [lacuna] 2-Trifluoromethyl-N-[(6-methoxy-2-methylpyrimidin-4-yl)carbonyl]benzylsulfonamide of melting point 120°-122° C.
  11. customis obtained in this way

Sources & evidence

ORD record
ord-fe210022b4274de48dbabedf1101f110
Source dataset
uspto-grants-1994_06
Patent number
US05324710

Reaction notes

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