Dimethylformamide → HCID 20515880, compound

HRID 1902215Notes

Reaction equation

HRID 1902215 reaction equation
[K].[OH:2][C:3]1[C:7]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)=[N:6][S:5](=[O:14])[N:4]=1.CN(C=O)C.[Cl:20][C:21]1[CH:29]=[CH:28][C:24]([C:25](Cl)=[O:26])=[CH:23][CH:22]=1.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[Cl:20][C:21]1[CH:29]=[CH:28][C:24]([C:25]([N:4]2[C:3](=[O:2])[C:7]([N:8]3[CH2:13][CH2:12][O:11][CH2:10][CH2:9]3)=[N:6][S:5]2=[O:14])=[O:26])=[CH:23][CH:22]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 85014-Chlorobenzoyl chlorideHCID 516892Sodium BicarbonateHCID 178527125HCID 178527125, compound

Product 1

HCID 20515880HCID 20515880, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a slurry of 2.3 grams of the potassium salt (C) from Example III(a) in 10 ml methylene chloride and 5 ml DMF is added 1.5 ml p-chlorobenzoylchloride. This mixture is allowed to stir for 1 hour at room temperature. After this, saturated sodium bicarbonate solution is added and the product is extracted into methylene chloride. The organic layer is dried and concentrated in vacuo. The crude product (E) is crystallized from ether and hexane to yield 2 grams of the title compound.

Workup

  1. extractionthe product is extracted into methylene chloride
  2. customThe organic layer is dried
  3. concentrationconcentrated in vacuo
  4. customThe crude product (E) is crystallized from ether and hexane

Sources & evidence

ORD record
ord-27680a8d11464c4e926c64ef7366b381
Source dataset
uspto-grants-1982_12
Patent number
US04362726

Reaction notes

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