1,3,2,4-Dithiadiphosphetane, 2,4-bis(methylthio)-, 2,4-disulfide → N-(1,1,3-trimethyl-4-indanyl)-2-methyl-4-trifluoromethylthiazole-5-carbothioamide

HRID 1904291Notes

Reaction equation

HRID 1904291 reaction equation
[CH3:1][C:2]1([CH3:25])[C:10]2[C:5](=[C:6]([NH:11][C:12]([C:14]3[S:18][C:17]([CH3:19])=[N:16][C:15]=3[C:20]([F:23])([F:22])[F:21])=O)[CH:7]=[CH:8][CH:9]=2)[CH:4]([CH3:24])[CH2:3]1.C[S:27]P1(=S)SP(=S)(SC)S1>O1CCCC1>[CH3:1][C:2]1([CH3:25])[C:10]2[C:5](=[C:6]([NH:11][C:12]([C:14]3[S:18][C:17]([CH3:19])=[N:16][C:15]=3[C:20]([F:23])([F:22])[F:21])=[S:27])[CH:7]=[CH:8][CH:9]=2)[CH:4]([CH3:24])[CH2:3]1

Participants

4

Reactant 2

HCID 45209581,3,2,4-Dithiadiphosphetane, 2,4-bis(methylthio)-, 2,4-disulfideHCID 14535764N-(1,1,3-trimethyl-4-indanyl)-2-methyl-4-trifluoromethylthiazole-5-carboxamide

Product 1

HCID 14535765N-(1,1,3-trimethyl-4-indanyl)-2-methyl-4-trifluoromethylthiazole-5-carbothioamideYield 67.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.20 g of N-(1,1,3-trimethyl-4-indanyl)-2-methyl-4-trifluoromethylthiazole-5-carboxamide and 0.18 g of 2,4-bis(methylthio)-1,3,2,4-dithiadiphosphetan-2,4-disulfide were dissolved in 5 ml of tetrahydrofuran and reaction was effected for 10 hours under reflux. The reaction mixture was concentrated and the residue was chromatographed on silica gel (eluent; n-hexane:chloroform:tetrahydrofuran=6:2:1) to obtain 0.14 g of N-(1,1,3-trimethyl-4-indanyl)-2-methyl-4-trifluoromethylthiazole-5-carbothioamide (yield 65%).

Workup

  1. customreaction
  2. temperatureunder reflux
  3. concentrationThe reaction mixture was concentrated
  4. customthe residue was chromatographed on silica gel (eluent; n-hexane:chloroform:tetrahydrofuran=6:2:1)

Sources & evidence

ORD record
ord-78d7c919130247e5932e7f3f5b64a276
Source dataset
uspto-grants-1989_06
Patent number
US04837242

Reaction notes

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