Isobutyryl chloride → N-Carbamothioyl-2-methylpropanamide

HRID 869394Notes

Reaction equation

HRID 869394 reaction equation
[NH2:1][C:2]([NH2:4])=[S:3].[C:5](Cl)(=[O:9])[CH:6]([CH3:8])[CH3:7]>C1(C)C=CC=CC=1>[C:5]([NH:1][C:2]([NH2:4])=[S:3])(=[O:9])[CH:6]([CH3:8])[CH3:7]

Participants

4

Reactant 2

HCID 62325Isobutyryl chlorideHCID 2723790Thiourea

Product 1

HCID 3555130N-Carbamothioyl-2-methylpropanamideYield 30.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Thiourea (152 g, 2 mol) was dissolved in toluene (1520 mL). To the solution was added isobutyryl chloride (213 g, 2 mol) under mechanical stirring. The reaction mixture was refluxed for 3 hours. TLC monitored the reaction. After the reaction completed, the reaction mixture was cooled to room temperature and filtered to remove insoluble solids. The filtrate was concentrated to dryness. The yellow solids were collected by filtration, washed with petroleum ether (100 mL×3) to appear white, dried in vacumm to give the desired product 11A (90 g, 30% yield) as a white solid (mp: 114˜116° C.).

Workup

  1. temperatureThe reaction mixture was refluxed for 3 hours
  2. customthe reaction
  3. filtrationfiltered
  4. customto remove insoluble solids
  5. concentrationThe filtrate was concentrated to dryness
  6. filtrationThe yellow solids were collected by filtration
  7. washwashed with petroleum ether (100 mL×3)
  8. customdried in vacumm

Sources & evidence

ORD record
ord-7ee250a5b8ca490791fd07500fa941c9
Source dataset
uspto-grants-2015_03
Patent number
US08969373B2

Reaction notes

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