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Triethylamine → 4-nitro-N-methyl-N-[2-(3-phenoxycarbonylaminoprop-1-yloxy)phenyl]benzamide

HRID 323136
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HRID 323136 반응식
[N+:1]([C:4]1[CH:24]=[CH:23][C:7]([C:8]([N:10]([CH3:22])[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[O:17][CH2:18][CH2:19][CH2:20][NH2:21])=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].C(N(CC)CC)C.Cl[C:33]([O:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)=[O:34]>ClCCl>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:8]([N:10]([CH3:22])[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[O:17][CH2:18][CH2:19][CH2:20][NH:21][C:33]([O:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[O:34])=[O:9])=[CH:23][CH:24]=1)([O-:3])=[O:2]
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참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 15891Phenyl chloroformateHCID 22011031HCID 22011031, 화합물

생성물 1

HCID 220105644-nitro-N-methyl-N-[2-(3-phenoxycarbonylaminoprop-1-yloxy)phenyl]benzamide수율 66.5%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

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온도
0 °C

실험 절차

To a solution of 4-nitro-N-methyl-N-[2-(3-aminoprop-1-yloxy)phenyl]benzamide (422 mg) and triethylamine (130 mg) in dichloromethane (10 ml) was added phenyl chloroformate (201 mg) and the solution was stirred at 0° C. for 30 minutes. The reaction mixture was diluted with dichloromethane and then the organic solution was washed successively with 1N hydrochloric acid, saturated sodium bicarbonate aqueous solution and brine. Drying, filtering and removal of solvents afforded a crude product. The crude product was chromatographed on silica gel (eluent; 1% methanol in chloroform) to give 4-nitro-N-methyl-N-[2-(3-phenoxycarbonylaminoprop-1-yloxy)phenyl]benzamide (383 mg) as a slightly yellow oil.

후처리

  1. washthe organic solution was washed successively with 1N hydrochloric acid, saturated sodium bicarbonate aqueous solution and brine
  2. customDrying
  3. filtrationfiltering
  4. customremoval of solvents
  5. customafforded a crude product
  6. customThe crude product was chromatographed on silica gel (eluent; 1% methanol in chloroform)

출처 및 근거

ORD 기록
ord-30c77ebe71df4912a7e0547dab416dfc
출처 데이터셋
uspto-grants-2001_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06211242B1

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