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

HRID 1607229ノート

反応式

HRID 1607229 の反応式
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

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 6342Acetonitrile溶媒2 回HCID 8471Triethylamine溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-0dbb9f569893467689776ebb88e09f1d
出典データセット
uspto-grants-1989_09
特許番号
US04863947

反応ノート

読み込み中…