Dimethylformamide → HCID 54157125, compound

HRID 1720566Notes

Reaction equation

HRID 1720566 reaction equation
[CH3:1][C:2]1[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][C:3]=1[O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12](=[N:16][O:17][CH3:18])[C:13](O)=[O:14].CN(C)C=O.S(Cl)([Cl:31])=O>C1(C)C=CC=CC=1>[CH3:1][C:2]1[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][C:3]=1[O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12](=[N:16][O:17][CH3:18])[C:13]([Cl:31])=[O:14]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 543974242-(2,5-Dimethylphenoxymethyl)-alpha-methoxyiminophenylacetic acid

Product 1

HCID 54157125HCID 54157125, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
60 °C

Procedure

2-[2-(2,5-Dimethylphenoxymethyl)phenyl]-2-methoxyiminoacetic acid (9.40 g, 30 mmol, E/Z=20/80) was dissolved in dimethylformamide (DMF)(0.11 g, 1.5 mmol) and toluene (20 ml). A solution of 95% thionyl chloride (4.13 g, 33 mmol) and toluene (10 ml) was added dropwise at 60° C. over 5 hours. The mixture was stirred at 60° C. for 5 hours. After completion of the reaction, the mixture was concentrated under reduced pressure to a total amount of 30 g to give crude 2-[2-(2,5-dimethylphenoxymethyl)phenyl]-2-methoxyiminoacetyl chloride.

Workup

  1. customAfter completion of the reaction
  2. concentrationthe mixture was concentrated under reduced pressure to a total amount of 30 g

Sources & evidence

ORD record
ord-da00d56f8c7b4b339a54539ba24fef70
Source dataset
uspto-grants-1996_04
Patent number
US05506358

Reaction notes

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