Thionyl Chloride → HCID 86584468, compound

HRID 2167431Notes

Reaction equation

HRID 2167431 reaction equation
[Cl:1][C:2]1[C:11]([C:12]([NH:14][CH2:15][CH:16]([CH3:19])[CH2:17]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][CH2:15][CH:16]([CH3:19])[CH2:17][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 86584469HCID 86584469, compound

Product 1

HCID 86584468HCID 86584468, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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

Workup

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

Sources & evidence

ORD record
ord-bc2db9591b4c433d835ada54c0d1a16e
Source dataset
uspto-grants-2015_06
Patent number
US09045465B1

Reaction notes

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