Oxalyl chloride → HCID 13881931, compound

HRID 543121Notes

Reaction equation

HRID 543121 reaction equation
[CH2:1]([N:3]([CH2:12][CH3:13])[C:4](=[O:11])[C:5]([CH3:10])([CH3:9])[C:6](O)=[O:7])[CH3:2].C(Cl)(=O)C([Cl:17])=O>C1C=CC=CC=1.CN(C)C=O>[CH2:1]([N:3]([CH2:12][CH3:13])[C:4](=[O:11])[C:5]([CH3:10])([CH3:9])[C:6]([Cl:17])=[O:7])[CH3:2]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 13881930HCID 13881930, compound

Product 1

HCID 13881931HCID 13881931, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalyst2×HCID 241BenzeneSolvent

Procedure

To a stirred suspension of the compound (1d) (6.6 g, 35.2 mmol) in benzene (25 ml) and freshly distilled oxalyl chloride (5.6 g, 44 mmol) was added at ambient temperature dimethylformamide (2 drops). After 1 hour at ambient temperature, additional dimethylformamide (2 drops) was added and the reaction mixture stirred for additional hour. The solvent was removed in vacuo to give a yellow liquid. The liquid was distilled at reduced pressure to give the desired product as a colorless liquid bp 74°-75° C. at 0.3 mmHg.

Workup

  1. customThe solvent was removed in vacuo
  2. customto give a yellow liquid
  3. distillationThe liquid was distilled at reduced pressure

Sources & evidence

ORD record
ord-d81ed5b2db354e0d8e1db54b2b5f1adc
Source dataset
uspto-grants-1987_04
Patent number
US04661483

Reaction notes

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