Ammonia → 2-Methyl-5-nitro-4-(4-o-tolyl-piperazin-1-yl)-benzamide

HRID 1481869

반응식

HRID 1481869 반응식
[CH3:1][C:2]1[CH:10]=[C:9]([N:11]2[CH2:16][CH2:15][N:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[CH3:23])[CH2:13][CH2:12]2)[C:8]([N+:24]([O-:26])=[O:25])=[CH:7][C:3]=1[C:4]([OH:6])=O.C(N1C=CN=C1)([N:29]1C=CN=C1)=O.N>ClCCl.C1COCC1.ClCCl.CO>[CH3:1][C:2]1[CH:10]=[C:9]([N:11]2[CH2:12][CH2:13][N:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[CH3:23])[CH2:15][CH2:16]2)[C:8]([N+:24]([O-:26])=[O:25])=[CH:7][C:3]=1[C:4]([NH2:29])=[O:6]

참가 물질

7

반응물 3

HCID 222AmmoniaHCID 682631,1'-CarbonyldiimidazoleHCID 896906482-Methyl-5-nitro-4-(4-o-tolyl-piperazin-1-yl)-benzoic acid

생성물 1

HCID 896905162-Methyl-5-nitro-4-(4-o-tolyl-piperazin-1-yl)-benzamide

시약·촉매·용매 3

HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매HCID 21226129Dichloromethane methanol용매

실험 절차

To a stirred solution of 2-methyl-5-nitro-4-(4-o-tolyl-piperazin-1-yl)-benzoic acid (6.2 g, 17.4 mmol) in anhydrous dichloromethane (170 mL), 1,1′-carbonyldiimidazole (7.07 g, 43.6 mmol) was added at 0° C. under N2 atmosphere. The reaction mixture was allowed to stir at room temperature for 2 h. Where upon a solution of ammonia in THF (≈4M) was added slowly at 0° C. under N2 atmosphere. The reaction mixture was allowed to stir at room temperature overnight. After the completion of the reaction as monitored by the TLC, solvent was removed in vacuo. Residue obtained was diluted with dichloromethane/methanol (150 mL, 9:1 by volume), and washed with water. Aqueous layer was again extracted in dichloromethane/methanol (3×50 mL). The combined extract was washed with brine solution and dried over anhydrous Na2SO4. The solvent was evaporated under reduced pressure to afford the pure product 2-methyl-5-nitro-4-(4-o-tolyl-piperazin-1-yl)-benzamide. Yield (6.0 g, 97%; and yellow solid).

후처리

  1. stirringto stir at room temperature overnight
  2. customAfter the completion of the reaction
  3. customwas removed in vacuo
  4. customResidue obtained
  5. washwashed with water
  6. extractionAqueous layer was again extracted in dichloromethane/methanol (3×50 mL)
  7. extractionThe combined extract
  8. washwas washed with brine solution
  9. dry with materialdried over anhydrous Na2SO4
  10. customThe solvent was evaporated under reduced pressure

출처 및 근거

ORD 기록
ord-02df728c3b0d4d23a221f71ec3244286
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09409897B2

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