Dimethylcarbamoyl Chloride → HCID 20322019, compound

HRID 436809Notes

Reaction equation

HRID 436809 reaction equation
[CH3:1][C:2]1[CH:10]=[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][N:4]2[N:3]=1.[Cl-].[Al+3].[Cl-].[Cl-].[K].[CH3:16][N:17]([CH3:21])[C:18](Cl)=[O:19]>>[CH3:16][N:17]([CH3:21])[C:18]([C:10]1[C:2]([CH3:1])=[N:3][N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12)=[O:19]

Participants

5

Reactant 4

HCID 6598Dimethylcarbamoyl ChlorideHCID 5462222PotassiumHCID 6451240Aluminum(III) ChlorideHCID 15620341HCID 15620341, compound

Product 1

HCID 20322019HCID 20322019, compoundYield 32.5%

Procedure

2-Methylpyrazolo[1,5-a]pyridine (3.6g) was dissolved in N,N-dimethylcarbamoyl chloride (10.8g). Aluminum chloride (8.0g) was added to the resulting solution and the mixture was heated at 130° for 3 hr and poured into ice water. The solution was made basic with potassium hydroxied solution and extracted with chloroform. The chloroform solution was dried over sodium sulfate and concentrated. The residue was distilled to give 1.8g of the objective product, bp 149°-150° (2 mmHg). Yield 32%.

Workup

  1. temperaturethe mixture was heated at 130° for 3 hr
  2. extractionextracted with chloroform
  3. dry with materialThe chloroform solution was dried over sodium sulfate
  4. concentrationconcentrated
  5. distillationThe residue was distilled

Sources & evidence

ORD record
ord-cad65eb8822a47a5be5ea0cc45517867
Source dataset
uspto-grants-1977_06
Patent number
US04028370

Reaction notes

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