Carbon Disulfide → HCID 54345874, compound

HRID 1253233Notes

Reaction equation

HRID 1253233 reaction equation
[C:1](=[S:3])=[S:2].[NH2:4][C:5]1[S:6][C:7]([C:10]([F:13])([F:12])[F:11])=[N:8][N:9]=1.Br[CH2:15][CH2:16][C:17]([F:21])=[C:18]([F:20])[F:19]>CS(C)=O>[F:11][C:10]([F:13])([F:12])[C:7]1[S:6][C:5]([NH:4][C:1](=[S:3])[S:2][CH2:15][CH2:16][C:17]([F:21])=[C:18]([F:20])[F:19])=[N:9][N:8]=1

Participants

5

Reactant 3

HCID 6348Carbon DisulfideHCID 663334-Bromo-1,1,2-trifluorobut-1-eneHCID 826341,3,4-Thiadiazol-2-amine, 5-(trifluoromethyl)-

Product 1

HCID 54345874HCID 54345874, compoundYield 33.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Carbon disulfide (5.78 grams, 0.076 mole) was added to a stirred solution of 2-amino-5-trifluoromethyl-1,3,4-thiadiazole (12.0 grams, 0.071 mole) in dimethyl sulfoxide (36 ml) under a nitrogen atmosphere. The reaction mixture was stirred for three hours at ambient temperature, then cooled to 0° C. at which time 4-bromo-1,1,2-trifluoro-1-butene (16.8 grams, 0.088 mole) was added dropwise. The reaction mixture was stirred at ambient temperature overnight. Crystals that had formed were collected by filtration, washed successively with petroleum ether and hexane and then dried, yielding 8.39 grams of (3,4,4-trifluoro-3-butenyl) N-(5-trifluoromethyl-1,3,4-thiadiazol-2-yl)-dithiocarbamate as a yellow powder. The NMR spectrum was consistent with the proposed structure.

Workup

  1. additionwas added dropwise
  2. stirringThe reaction mixture was stirred at ambient temperature overnight
  3. customCrystals that had formed
  4. filtrationwere collected by filtration
  5. washwashed successively with petroleum ether and hexane
  6. customdried

Sources & evidence

ORD record
ord-0a93a8a12a35464ca7392f8703033a86
Source dataset
uspto-grants-1988_05
Patent number
US04748186

Reaction notes

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