Dimethylformamide → HCID 22131317, compound

HRID 1857573Notes

Reaction equation

HRID 1857573 reaction equation
[CH3:1][CH:2]([S:4]([NH2:7])(=[O:6])=[O:5])[CH3:3].CN(C)C=O.[H-].[Na+].[Cl:15][C:16]1[CH:17]=[C:18]([N:23]=[C:24]=[O:25])[CH:19]=[CH:20][C:21]=1[Cl:22]>C1COCC1>[Cl:15][C:16]1[CH:17]=[C:18]([NH:23][C:24]([NH:7][S:4]([CH:2]([CH3:3])[CH3:1])(=[O:6])=[O:5])=[O:25])[CH:19]=[CH:20][C:21]=1[Cl:22]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 76073,4-Dichlorophenyl isocyanateHCID 24758Sodium hydrideHCID 3549191Propane-2-sulfonamide

Product 1

HCID 22131317HCID 22131317, compoundYield 44.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

2-propanesulfonamide (4.40 g) was combined with THF (150 ml) and then dimethylformamide (40 ml) and sodium hydride (2.1 g) were added and the mixture stirred two hours at room temperature. To the mixture was added 3,4-dichlorophenyl isocyanate (7.52 g) in THF (50 ml) and the mixture stirred overnight. The solvent was removed under vacuum, water was added and the mixture filtered. The filtrate was evaporated and then more water introduced when crystals did not form. The solution was made acidic and stirred overnight. The precipitated solid was recovered by filtration. Recrystallization from toluene provided 4.9 g of product with a melting point 151-4° C.

Workup

  1. stirringthe mixture stirred overnight
  2. customThe solvent was removed under vacuum, water
  3. additionwas added
  4. filtrationthe mixture filtered
  5. customThe filtrate was evaporated
  6. additionmore water introduced when crystals
  7. stirringstirred overnight
  8. filtrationThe precipitated solid was recovered by filtration
  9. customRecrystallization from toluene

Sources & evidence

ORD record
ord-1b6ef2fccaad4cac9497e7b759f10281
Source dataset
uspto-grants-2000_11
Patent number
US06147115

Reaction notes

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