Dichloromethane → 5-[(2,4-Dioxo-1,3-thiazolidin-5-yl)methyl]-2-methoxy-N-{[4-(trifluoromethyl)phenyl]methyl}benzamide

HRID 1834999노트

반응식

HRID 1834999 반응식
ClCCl.[O:4]=[C:5]1[NH:9][C:8](=[O:10])[CH:7]([CH2:11][C:12]2[CH:13]=[CH:14][C:15]([O:21][CH3:22])=[C:16]([CH:20]=2)[C:17]([OH:19])=O)[S:6]1.C(Cl)(=O)OCC.[F:29][C:30]([F:40])([F:39])[C:31]1[CH:38]=[CH:37][C:34]([CH2:35][NH2:36])=[CH:33][CH:32]=1>C(N(CC)CC)C>[O:4]=[C:5]1[NH:9][C:8](=[O:10])[CH:7]([CH2:11][C:12]2[CH:13]=[CH:14][C:15]([O:21][CH3:22])=[C:16]([CH:20]=2)[C:17]([NH:36][CH2:35][C:34]2[CH:33]=[CH:32][C:31]([C:30]([F:29])([F:39])[F:40])=[CH:38][CH:37]=2)=[O:19])[S:6]1

참가 물질

6

반응물 4

HCID 6344DichloromethaneHCID 10928Ethyl chloroformateHCID 768044-(Trifluoromethyl)benzylamineHCID 9943613HCID 9943613, 화합물

생성물 1

HCID 1511835-[(2,4-Dioxo-1,3-thiazolidin-5-yl)methyl]-2-methoxy-N-{[4-(trifluoromethyl)phenyl]methyl}benzamide수율 61.3%

시약·촉매·용매 1

HCID 8471Triethylamine용매

실험 절차

To 49 mL of dichloromethane were added 6.30 g of triethylamine and 7.00 g of 5-[(2,4-dioxothiazolidin-5-yl) methyl]-2-methoxybenzoic acid. After 2.71 g of ethyl chlorocarbonate were added, the mixture was stirred for 10 minutes. Further, 4.59 g of 4-trifluoromethylbenzylamine were added and the mixture was stirred for 1 hour. After washed the reaction mixture with water, solvent was distilled off and to the residue were added 109 mL of water and 33 mL of ethanol, to which solution 2 mol/L hydrochloric acid was added dropwise to adjust to pH 2.0. The precipitated crystals were collected by filtration and washed with water to obtain 10.25 g of crude crystals. By recrystallizing 10.25 g of crude crystals twice from 90% ethanol, 6.49 g of 5-[(2,4-dioxothiazolidin-5-yl) methyl]-2-methoxy-N-[[4-(trifluoromethyl)phenyl]methyl] benzamide (KRP-297) were obtained (yield 61.3%).

후처리

  1. stirringthe mixture was stirred for 1 hour
  2. washAfter washed the reaction mixture with water, solvent
  3. distillationwas distilled off and to the residue
  4. additionwere added 109 mL of water and 33 mL of ethanol
  5. additionto which solution 2 mol/L hydrochloric acid was added dropwise
  6. filtrationThe precipitated crystals were collected by filtration
  7. washwashed with water
  8. customto obtain 10.25 g of crude crystals
  9. customBy recrystallizing 10.25 g of crude crystals twice from 90% ethanol

출처 및 근거

ORD 기록
ord-5edc02e5500e46db913ed432caf4337b
출처 데이터셋
uspto-grants-2004_08
특허 번호
US06770133B2

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