Dichloromethane → HCID 19791567, compound

HRID 1655278Notes

Reaction equation

HRID 1655278 reaction equation
O[CH:2]([C:6]1[C:7]([O:12][CH3:13])=[N:8][CH:9]=[CH:10][CH:11]=1)[CH2:3][CH:4]=[CH2:5].[Cl:14]CCl.S(Cl)(Cl)=O>>[Cl:14][CH:2]([C:6]1[C:7]([O:12][CH3:13])=[N:8][CH:9]=[CH:10][CH:11]=1)[CH2:3][CH:4]=[CH2:5]

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 24386Thionyl ChlorideHCID 19791572HCID 19791572, compound

Product 1

HCID 19791567HCID 19791567, compoundYield 94%

Procedure

56.5 g (0.32 mol) of the compound from Example I are stirred in 400 ml of anhydrous dichloromethane containing 277 ml (3.8 mol) of thionyl chloride overnight at 20°-30° C. Subsequently, dichloromethane and unreacted thionyl chloride are removed in a water pump vacuum at 20°-30° C. The residue is partitioned between dichloromethane and aqueous saturated sodium bicarbonate solution. The organic phase is separated off, dried and evaporated in vacuo. 59.3 g of the crude title compound are obtained as an oil.

Workup

  1. customSubsequently, dichloromethane and unreacted thionyl chloride are removed in a water pump vacuum at 20°-30° C
  2. customThe residue is partitioned between dichloromethane and aqueous saturated sodium bicarbonate solution
  3. customThe organic phase is separated off
  4. customdried
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-4233e578600b496db847cab40d77b137
Source dataset
uspto-grants-1993_10
Patent number
US05250540

Reaction notes

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