Phosgene → N-(5-chloropyrid-2-yl)-3-(4-chlorophenyl)-4-carbomethoxy-4-methyl-4,5-dihydro-1H-pyrazole-1-carboxamide

HRID 1607229노트

반응식

HRID 1607229 반응식
C(Cl)(Cl)=O.Cl.[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[C:17]([C:19]([O:21][CH3:22])=[O:20])([CH3:18])[CH2:16][NH:15][N:14]=2)=[CH:9][CH:8]=1.[C:23](Cl)(=[O:25])[NH2:24].N[C:28]1[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][N:29]=1>C(OCC)(=O)C.C(N(CC)CC)C.C(#N)C>[Cl:34][C:31]1[CH:32]=[CH:33][C:28]([NH:24][C:23]([N:15]2[CH2:16][C:17]([C:19]([O:21][CH3:22])=[O:20])([CH3:18])[C:13]([C:10]3[CH:9]=[CH:8][C:7]([Cl:6])=[CH:12][CH:11]=3)=[N:14]2)=[O:25])=[N:29][CH:30]=1

참가 물질

8

반응물 4

HCID 6371PhosgeneHCID 661742-Amino-5-chloropyridineHCID 68048Carbamic chlorideHCID 198521223-(4-chlorophenyl)-4-carbomethoxy-4-methyl-4,5-dihydro-1H-pyrazole hydrochloride

생성물 1

HCID 19852657N-(5-chloropyrid-2-yl)-3-(4-chlorophenyl)-4-carbomethoxy-4-methyl-4,5-dihydro-1H-pyrazole-1-carboxamide

시약·촉매·용매 3

HCID 6342Acetonitrile용매2회HCID 8471Triethylamine용매2회HCID 8857Ethyl Acetate용매

실험 절차

To 10 ml of acetonitrile containing 4.5 ml of 2.5M phosgene in ethyl acetate was added a slurry of 2.9 g (10 mmole) of 3-(4-chlorophenyl)-4-carbomethoxy-4-methyl-4,5-dihydro-1H-pyrazole hydrochloride 2.0 g (20 mmole) of triethylamine and 20 ml of acetonitrile. After stirring for 10 minutes the carbamoyl chloride was judged to have been formed and then 1.5 g (11 mmole) of 2-amino-5-chloropyridine was added with an additional 2 g of triethylamine. After stirring for 18 hours the mixture was partitioned between ether and water, washed with brine, dried over magnesium sulfate, filtered concentrated, and chromatographed yielding N-(5-chloropyrid-2-yl)-3-(4-chlorophenyl)-4-carbomethoxy-4-methyl-4,5-dihydro-1H-pyrazole-1-carboxamide, mp 130°-146° C. NMR data was consistent with the structure.

후처리

  1. customto have been formed
  2. customwas partitioned between ether and water
  3. washwashed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customchromatographed

출처 및 근거

ORD 기록
ord-0dbb9f569893467689776ebb88e09f1d
출처 데이터셋
uspto-grants-1989_09
특허 번호
US04863947

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