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

HRID 2419570Notes

Reaction equation

HRID 2419570 reaction equation
[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]

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-352d71ab6e3e430ebddb6a92b9110eab
Source dataset
uspto-grants-1978_08
Patent number
US04107175

Reaction notes

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