3-(Trifluoromethyl)benzaldehyde → 3-[(1,3-Benzodithiol-2-ylidene)amino]-2-thioxo-5-[[3-(trifluoromethyl)phenyl]methylene]-4-thiazolidinone

HRID 2419570노트

반응식

HRID 2419570 반응식
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[S:3][C:2]1=[N:10][N:11]1[C:15](=[O:16])[CH2:14][S:13][C:12]1=[S:17].[F:18][C:19]([F:29])([F:28])[C:20]1[CH:21]=[C:22]([CH:25]=[CH:26][CH:27]=1)[CH:23]=O.C(O)(=O)C.N1CCCCC1>C(COC)OC.ClCCl>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[S:3][C:2]1=[N:10][N:11]1[C:15](=[O:16])[C:14](=[CH:23][C:22]2[CH:25]=[CH:26][CH:27]=[C:20]([C:19]([F:18])([F:28])[F:29])[CH:21]=2)[S:13][C:12]1=[S:17]

참가 물질

6

반응물 3

HCID 679903-(Trifluoromethyl)benzaldehydeHCID 9793820Piperidine, acetateHCID 124949933-[(1,3-Benzodithiol-2-ylidene)amino]-2-thioxo-4-thiazolidinone

생성물 1

HCID 541307973-[(1,3-Benzodithiol-2-ylidene)amino]-2-thioxo-5-[[3-(trifluoromethyl)phenyl]methylene]-4-thiazolidinone

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 80711,2-Dimethoxyethane용매

실험 절차

A slurry of 3-[(1,3-benzodithiol-2-ylidene)amino]-2 -thioxo-4-thiazolidinone (see example 37), m-trifluoromethylbenzaldehyde (10 ml, excess) and acetic acid/piperidine (1 ml) in 250 ml of anhydrous glyme is heated at reflux for seven days. The reaction mixture is concentrated in vacuo and the oily residue extracted with hexane. The solid thus obtained is slurried in 1000 ml of dichloromethane and stirred at room temperature overnight. The slurry is filtered and the filtrate concentrated in vacuo. The solid residue thus obtained is recrystallized from dimethylformamide to yield 500 mg of the title compound, melting point 268°-269° C.

후처리

  1. temperatureat reflux for seven days
  2. concentrationThe reaction mixture is concentrated in vacuo
  3. extractionthe oily residue extracted with hexane
  4. customThe solid thus obtained
  5. filtrationThe slurry is filtered
  6. concentrationthe filtrate concentrated in vacuo
  7. customThe solid residue thus obtained
  8. customis recrystallized from dimethylformamide

출처 및 근거

ORD 기록
ord-352d71ab6e3e430ebddb6a92b9110eab
출처 데이터셋
uspto-grants-1978_08
특허 번호
US04107175

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