Chloroacetyl chloride → Methyl 1-(Chloroacetyl)-4-(4-methoxybenzenesulfonyl)-2,3,4,5-tetrahydro-1H-[1,4]benzodiazepine-3-carboxylate

HRID 1420628노트

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HRID 1420628 반응식
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:12]2[CH2:18][C:17]3[CH:19]=[CH:20][CH:21]=[CH:22][C:16]=3[NH:15][CH2:14][CH:13]2[C:23]([O:25][CH3:26])=[O:24])(=[O:11])=[O:10])=[CH:5][CH:4]=1.C(N(CC)CC)C.[Cl:34][CH2:35][C:36](Cl)=[O:37]>C(Cl)Cl.O>[Cl:34][CH2:35][C:36]([N:15]1[C:16]2[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=2[CH2:18][N:12]([S:9]([C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)(=[O:10])=[O:11])[CH:13]([C:23]([O:25][CH3:26])=[O:24])[CH2:14]1)=[O:37]

참가 물질

6

반응물 3

HCID 6577Chloroacetyl chloride2회HCID 8471Triethylamine2회HCID 18612753Methyl 4-(4-Methoxybenzenesulfonyl)-2,3,4,5-tetrahydro-1H-[1,4]benzodiazepine-3-carboxylate

생성물 1

HCID 18612717Methyl 1-(Chloroacetyl)-4-(4-methoxybenzenesulfonyl)-2,3,4,5-tetrahydro-1H-[1,4]benzodiazepine-3-carboxylate수율 24.9%

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매2회

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온도
0 °C

실험 절차

To a mixture of 2.5 g (6.64 mmol) of methyl 4-(4-methoxybenzenesulfonyl)-2,3,4,5-tetrahydro-1H-[1,4]benzodiazepine-3-carboxylate (Reference Example 12) and 4.63 ml (33.2 mmol) of triethylamine in 40 ml of CH2Cl2 cooled to 0° C. was added to 1.65 g (14.63 mmol) of chloroacetyl chloride. The solution was stirred at room temperature for 2 days, chilled to 0° C. and 926 μl of triethylamine and 750 mg of chloroacetyl chloride were added thereto. The mixture was stirred at room temperature overnight, diluted with CH2Cl2 and H2O. The insoluble solid was filtered off. The organic layer of the filtrate was separated , washed with brine, dried with Na2SO4 and filtered through diatomaceous earth. The solvent was removed and the residue triturated with ethyl acetate and a trace of ethanol. Chilling and filtering gave 0.75 g of methyl 1-(chloroacetyl)-4-(4-methoxybenzenesulfonyl)-2,3,4,5-tetrahydro-1H-[1,4]benzo-diazepine-3-carboxylate (Reference Example 91). Anal. for C2OH21ClN2O6S: Calc'd: C,53.0; H,4.7; N,6.2; Found: C,51.6; H,4.6; N,5.7; Mass Spectrum (ES): 453.0 (M+H).

후처리

  1. temperaturechilled to 0° C.
  2. stirringThe mixture was stirred at room temperature overnight
  3. filtrationThe insoluble solid was filtered off
  4. customThe organic layer of the filtrate was separated
  5. washwashed with brine
  6. dry with materialdried with Na2SO4
  7. filtrationfiltered through diatomaceous earth
  8. customThe solvent was removed
  9. customthe residue triturated with ethyl acetate
  10. temperatureChilling
  11. filtrationfiltering

출처 및 근거

ORD 기록
ord-efb48a526af1409bb9dd1b74618737e5
출처 데이터셋
uspto-grants-2000_06
특허 번호
US06071903

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