Thionyl Chloride → HCID 54043231, compound

HRID 1276121Notes

Reaction equation

HRID 1276121 reaction equation
[Cl:1][C:2]1[C:11]([C:12]([NH:14][C:15]([CH3:19])([CH3:18])[CH2:16]O)=[O:13])=[C:10]([S:20]([CH3:23])(=[O:22])=[O:21])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].S(Cl)([Cl:26])=O>ClCCl>[Cl:1][C:2]1[C:11]([C:12]([NH:14][C:15]([CH3:19])([CH3:18])[CH2:16][Cl:26])=[O:13])=[C:10]([S:20]([CH3:23])(=[O:22])=[O:21])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 54279457HCID 54279457, compound

Product 1

HCID 54043231HCID 54043231, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 6.9 g (20 mmol) of methyl 2-chloro-3-(1-hydroxy-2,2-dimethyleth-2-ylaminocarbonyl)-4-methylsulfonylbenzoate and 5 ml of thionyl chloride was stirred at room temperature for 6 hours. The solution was diluted with 50 ml of dichloromethane and subsequently concentrated. The residue was dissolved in 20 ml of dichloromethane. Addition of cyclohexane resulted in the formation of a crystalline precipitate which was filtered off with suction and dried. 6.4 g (88% of theory) of methyl 2-chloro-3-(1-chloro-2,2-dimethyleth-2-ylaminocarbonyl)-4-methylsulfonylbenzoate were obtained.

Workup

  1. concentrationsubsequently concentrated
  2. dissolutionThe residue was dissolved in 20 ml of dichloromethane
  3. additionAddition of cyclohexane
  4. customresulted in the formation of a crystalline precipitate which
  5. filtrationwas filtered off with suction
  6. customdried

Sources & evidence

ORD record
ord-583204c3f22a40b3a067bc786f34f698
Source dataset
uspto-grants-2000_12
Patent number
US06165944

Reaction notes

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