Dimethylformamide → HCID 88735857, compound

HRID 1074551Notes

Reaction equation

HRID 1074551 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][C:24]=1[Cl:25])[CH2:5][N:6]1[N:15]=[C:14]([C:16](O)=[O:17])[C:13]2[C:8](=[CH:9][C:10]([O:19][CH3:20])=[CH:11][CH:12]=2)[C:7]1=[O:21].CN(C)C=O.S(Cl)([Cl:33])=O>>[Cl:1][C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][C:24]=1[Cl:25])[CH2:5][N:6]1[N:15]=[C:14]([C:16]([Cl:33])=[O:17])[C:13]2[C:8](=[CH:9][C:10]([O:19][CH3:20])=[CH:11][CH:12]=2)[C:7]1=[O:21]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 20495804HCID 20495804, compound

Product 1

HCID 88735857HCID 88735857, compound

Procedure

A stirred mixture of 2-(3,4-dichlorobenzyl)-7-methoxy-1,2-dihydro-1-oxophthalazin-4-ylcarboxylic acid (1.9 g.) in thionyl chloride (10 ml.) containing dimethylformamide (0.1 ml.) was heated under reflux for 3 hours. The solution obtained was then evaporated. The residue was dissolved in dry toluene and the solution evaporated. This procedure was carried out three times to give 2-(3,4-dichlorobenzyl)-7-methoxy-1,2-dihydro-1-oxophthalazin-4-ylcarboxylic acid chloride in essentially quantitative yield as a solid, having a satisfactory IR spectrum.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 3 hours
  3. customThe solution obtained
  4. customwas then evaporated
  5. dissolutionThe residue was dissolved in dry toluene
  6. customthe solution evaporated

Sources & evidence

ORD record
ord-be486695dcb044dda93b884835b66936
Source dataset
uspto-grants-1983_07
Patent number
US04393062

Reaction notes

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