Thionyl Chloride → HCID 21823971, compound

HRID 1576087Notes

Reaction equation

HRID 1576087 reaction equation
[CH2:1]([NH:5][C:6]1[C:11]([C:12](O)=[O:13])=[CH:10][N:9]=[C:8]2[N:15]([CH2:18][CH3:19])[N:16]=[CH:17][C:7]=12)[CH2:2][CH2:3][CH3:4].S(Cl)([Cl:22])=O>>[CH2:1]([NH:5][C:6]1[C:11]([C:12]([Cl:22])=[O:13])=[CH:10][N:9]=[C:8]2[N:15]([CH2:18][CH3:19])[N:16]=[CH:17][C:7]=12)[CH2:2][CH2:3][CH3:4]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 21823970HCID 21823970, compound

Product 1

HCID 21823971HCID 21823971, compound

Procedure

26.2 g of 4-butylamino-1-ethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid (0.1 mol) and 100 ml of thionyl chloride are refluxed for 4 hours. The thionyl chloride is removed by means of a water aspirator. The residue, containing the crude 4-butyl-amino-1-ethyl-1H-pyrazolo[3,4-b]pyridine-5-carbonyl chloride, is recrystallized from benzene, and has a melting point of 142°-145°. Yield 23.5 g = 84% of theory.

Workup

  1. customThe thionyl chloride is removed by means of a water aspirator
  2. additionThe residue, containing the crude 4-butyl-amino-1-ethyl-1H-pyrazolo[3,4-b]pyridine-5-carbonyl chloride
  3. customis recrystallized from benzene

Sources & evidence

ORD record
ord-77c54833375d41ef858a129a8572d6d4
Source dataset
uspto-grants-1976_09
Patent number
US03979399

Reaction notes

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