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Toluene → 3-Dimethylcarbamoyl-4-methoxy-5-trifluoromethylbenzoyl chloride

HRID 385110
Notes
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Reaction equation

HRID 385110 reaction equation
[CH3:1][N:2]([CH3:20])[C:3]([C:5]1[CH:6]=[C:7]([CH:11]=[C:12]([C:16]([F:19])([F:18])[F:17])[C:13]=1[O:14][CH3:15])[C:8](O)=[O:9])=[O:4].C1(C)C=CC=CC=1.S(Cl)([Cl:30])=O>CN(C)C=O>[CH3:1][N:2]([CH3:20])[C:3]([C:5]1[CH:6]=[C:7]([CH:11]=[C:12]([C:16]([F:19])([F:18])[F:17])[C:13]=1[O:14][CH3:15])[C:8]([Cl:30])=[O:9])=[O:4]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 1140TolueneHCID 24386Thionyl ChlorideHCID 68108962HCID 68108962, compound

Product 1

HCID 866681743-Dimethylcarbamoyl-4-methoxy-5-trifluoromethylbenzoyl chloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To 3-dimethylcarbamoyl-4-methoxy-5-trifluoromethylbenzoic acid (333 mg), toluene (3 mL), N,N-dimethylformamide (1 droplet) and thionyl chloride (0.13 mL) was added, and then the mixture was stirred at 60° C. for 6 hours. The solvent was distilled off under reduced pressure and the obtained residue was azeotroped with toluene and used for the synthesis of (f).

Workup

  1. distillationThe solvent was distilled off under reduced pressure
  2. customthe obtained residue was azeotroped with toluene
  3. customused for the synthesis of (f)

Sources & evidence

ORD record
ord-28fb25fc478a40868eeda7a53e8bf313
Source dataset
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08367843B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes