Carbon Disulfide → (3,4,4-trifluoro-3-butenyl) N-(2,3-dihydro-2,2-dimethylbenzofuran-7-yl)dithiocarbamate

HRID 1253232Notes

Reaction equation

HRID 1253232 reaction equation
[OH-].[Na+].[NH2:3][C:4]1[C:12]2[O:11][C:10]([CH3:14])([CH3:13])[CH2:9][C:8]=2[CH:7]=[CH:6][CH:5]=1.[C:15](=[S:17])=[S:16].Br[CH2:19][CH2:20][C:21]([F:25])=[C:22]([F:24])[F:23]>CS(C)=O.O>[CH3:13][C:10]1([CH3:14])[CH2:9][C:8]2[CH:7]=[CH:6][CH:5]=[C:4]([NH:3][C:15](=[S:17])[S:16][CH2:19][CH2:20][C:21]([F:25])=[C:22]([F:24])[F:23])[C:12]=2[O:11]1

Participants

7

Reactant 4

HCID 6348Carbon DisulfideHCID 14798Sodium HydroxideHCID 663334-Bromo-1,1,2-trifluorobut-1-eneHCID 916972,2-Dimethyl-2,3-dihydro-1-benzofuran-7-amine

Product 1

HCID 53946512(3,4,4-trifluoro-3-butenyl) N-(2,3-dihydro-2,2-dimethylbenzofuran-7-yl)dithiocarbamate

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

Sodium hydroxide (3.7 ml, 20M) was added to a stirred solution of 7-amino-2,3-dihydro-2,2-dimethylbenzofuran (10 grams, 0.061 mole) in dimethyl sulfoxide (31 ml). Upon completion of addition, carbon disulfide (6.06 grams, 0.08 mole) was added. The reaction mixture was stirred for one hour at ambient temperature, then cooled to 0° C. at which time 4-bromo-1,1,2-trifluoro-1-butene was added dropwise. The reaction mixture was stirred at ambient temperature overnight. The reaction mixture was diluted with water (400 ml) and extracted with diethyl ether. The extract was dried (sodium sulfate) and concentrated under reduced pressure leaving a residue. This residue was passed through a column of silica gel, eluting with hexane:diethyl ether (9:1). Appropriate fractions were combined and concentrated under reduced pressure, yielding (3,4,4-trifluoro-3-butenyl) N-(2,3-dihydro-2,2-dimethylbenzofuran-7-yl)dithiocarbamate (Compound A12). The NMR spectrum was consistent with the proposed structure.

Workup

  1. additionwas added
  2. additionwas added dropwise
  3. stirringThe reaction mixture was stirred at ambient temperature overnight
  4. extractionextracted with diethyl ether
  5. dry with materialThe extract was dried (sodium sulfate)
  6. concentrationconcentrated under reduced pressure
  7. customleaving a residue
  8. washeluting with hexane:diethyl ether (9:1)
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1a660b4b04bf4134843eb28e79896b52
Source dataset
uspto-grants-1988_05
Patent number
US04748186

Reaction notes

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