Hydrochloric Acid → N-[2-(2-ethoxyethoxy)-phenyl-sulfonyl]-N'-(4-difluoromethoxy-6-methylpyrimidin-2-yl)-urea
Reaction equation
N12CCCCC1C=NCCC2.O([C:19]([NH:21][C:22]1[N:27]=[C:26]([O:28][CH:29]([F:31])[F:30])[CH:25]=[C:24]([CH3:32])[N:23]=1)=[O:20])C1C=CC=CC=1.[CH2:33]([O:35][CH2:36][CH2:37][O:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=1[S:45]([NH2:48])(=[O:47])=[O:46])[CH3:34].Cl>C(#N)C.O.C(OCC)(=O)C>[CH2:33]([O:35][CH2:36][CH2:37][O:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=1[S:45]([NH:48][C:19]([NH:21][C:22]1[N:27]=[C:26]([O:28][CH:29]([F:30])[F:31])[CH:25]=[C:24]([CH3:32])[N:23]=1)=[O:20])(=[O:46])=[O:47])[CH3:34]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Procedure
1.8 g (0.012 mol) of 1,5-diazabicyclo(5.4.0)undec-5-ene are added to a solution of 3.5 g (0.012 mol) of 2-phenoxycarbonylamino-4-difluoromethoxy-6-methyl-pyrimidine, in the form of the crude product, and 2.9 g (0.012 mol) of 2-(2-ethoxy-ethoxy)-benzenesulfonamide in 100 ml of absolute acetonitrile and the mixture is stirred at 20°-25° C. for 1 hour and then diluted with 500 ml of water and acidified with hydrochloric acid. The oil which separates out is taken up in 200 ml of ethyl acetate and the mixture is dried over sodium sulfate and evaporated. The oily residue is crystallised from diethyl ether and acetone to give N-[2-(2-ethoxy-ethoxy)-phenyl-sulfonyl]-N'-(4-difluoromethoxy-6-methyl-pyrimidin-2-yl)-urea of melting point 90°-95° C. (decomposition) as colourless crystals in a yield of 2.7 g.
Workup
- dry with materialthe mixture is dried over sodium sulfate
- customevaporated
- customThe oily residue is crystallised from diethyl ether and acetone
Sources & evidence
- ORD record
- ord-31aa5dd2a6994bfeafd356aaecbe9747
- Source dataset
- uspto-grants-1987_09
- Patent number
- US04693741
Reaction notes
Loading…