Methyl isothiocyanate → 5-(2-methylaminothiocarbonylaminoethoxy)-7-chloro-1-[2-methoxy-4-(2-chlorobenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzoazepine

HRID 1291554

반응식

HRID 1291554 반응식
[CH3:1][N:2]=[C:3]=[S:4].[NH2:5][CH2:6][CH2:7][O:8][CH:9]1[C:15]2[CH:16]=[C:17]([Cl:20])[CH:18]=[CH:19][C:14]=2[N:13]([C:21](=[O:40])[C:22]2[CH:27]=[CH:26][C:25]([NH:28][C:29](=[O:37])[C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[Cl:36])=[CH:24][C:23]=2[O:38][CH3:39])[CH2:12][CH2:11][CH2:10]1>C(O)C>[CH3:1][NH:2][C:3]([NH:5][CH2:6][CH2:7][O:8][CH:9]1[C:15]2[CH:16]=[C:17]([Cl:20])[CH:18]=[CH:19][C:14]=2[N:13]([C:21](=[O:40])[C:22]2[CH:27]=[CH:26][C:25]([NH:28][C:29](=[O:37])[C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[Cl:36])=[CH:24][C:23]=2[O:38][CH3:39])[CH2:12][CH2:11][CH2:10]1)=[S:4]

참가 물질

4

반응물 2

HCID 11167Methyl isothiocyanateHCID 189172105-(2-aminoethoxy)-7-chloro-1-[2-methoxy-4-(2-chlorobenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzoazepine

생성물 1

HCID 220716315-(2-methylaminothiocarbonylaminoethoxy)-7-chloro-1-[2-methoxy-4-(2-chlorobenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzoazepine

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

0.13 ml of methyl isothiocyanate was added to 20 ml of a suspension of 0.5 g of 5-(2-aminoethoxy)-7-chloro-1-[2-methoxy-4-(2-chlorobenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzoazepine in ethanol. The mixture was refluxed for 3 hours. The reaction mixture was subjected to vacuum distillation to remove ethanol. The residue was mixed with a saturated aqueous sodium hydrogencarbonate solution, followed by extraction with ethyl acetate. The organic layer was dried over magnesium sulfate and then subjected to vacuum distillation to remove the solvent. The residue was purified by silica gel column chromatography (elutant: dichloromethane/methanol=50/1) to obtain 0.46 g of 5-(2-methylaminothiocarbonylaminoethoxy)-7-chloro-1-[2-methoxy-4-(2-chlorobenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzoazepine.

후처리

  1. temperatureThe mixture was refluxed for 3 hours
  2. distillationThe reaction mixture was subjected to vacuum distillation
  3. customto remove ethanol
  4. additionThe residue was mixed with a saturated aqueous sodium hydrogencarbonate solution
  5. extractionfollowed by extraction with ethyl acetate
  6. dry with materialThe organic layer was dried over magnesium sulfate
  7. distillationsubjected to vacuum distillation
  8. customto remove the solvent
  9. customThe residue was purified by silica gel column chromatography (elutant: dichloromethane/methanol=50/1)

출처 및 근거

ORD 기록
ord-c88e452fcdcc4ac4b112ac52640a941a
출처 데이터셋
uspto-grants-1998_05
특허 번호
US05753644

연결된 노트

불러오는 중…