Water → HCID 54091611, compound

HRID 2352676Notes

Reaction equation

HRID 2352676 reaction equation
[H-].[Na+].[CH3:3][N:4]([CH3:8])[C:5](Cl)=[O:6].[F:9][C:10]([S:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[CH:11][CH2:12][OH:13].O>C1COCC1.CN(P(N(C)C)(N(C)C)=O)C>[CH3:3][N:4]([CH3:8])[C:5](=[O:6])[O:13][CH2:12][CH:11]=[C:10]([F:9])[S:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]

Participants

7

Reactant 4

HCID 962WaterHCID 6598Dimethylcarbamoyl ChlorideHCID 24758Sodium hydrideHCID 54174844HCID 54174844, compound

Product 1

HCID 54091611HCID 54091611, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 12679HexamethylphosphoramideSolvent

Procedure

To a slurry of sodium hydride (125 mg, 5.2 mmol) in 5 ml of THF and 2 ml of HMPA under N2 is added dimethylcarbamoyl chloride (0.37 ml, 430 mg, 4.0 mmol). The slurry is cooled in an ice bath and 3-fluoro-3-hexylthio-2-propen-1-ol (450 mg, 2.34 mmol) is added gradually. After 1 hour, the mixture is cautiously poured into water, extracted with ether and stripped to give 3-fluoro-3-hexylthio-2-propenyl dimethylcarbamate.

Workup

  1. temperatureThe slurry is cooled in an ice bath
  2. extractionextracted with ether

Sources & evidence

ORD record
ord-0fd492ac78704152b6f31a36e8d0d288
Source dataset
uspto-grants-1989_10
Patent number
US04877899

Reaction notes

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