2-Propoxybenzoyl chloride → HCID 178458320, compound

HRID 1837550Notes

Reaction equation

HRID 1837550 reaction equation
[CH2:1]([O:4][C:5]1[CH:13]=[CH:12][CH:11]=[CH:10][C:6]=1[C:7](Cl)=[O:8])[CH2:2][CH3:3].[NH2:14][C:15]1[C:16]([CH2:23][CH2:24][CH3:25])=[N:17][NH:18][C:19]=1[C:20]([NH2:22])=[O:21]>ClCCl.N1C=CC=CC=1>[CH2:1]([O:4][C:5]1[CH:13]=[CH:12][CH:11]=[CH:10][C:6]=1[C:7]([NH:14][C:15]1[C:16]([CH2:23][CH2:24][CH3:25])=[N:17][NH:18][C:19]=1[C:20]([NH2:22])=[O:21])=[O:8])[CH2:2][CH3:3]

Participants

5

Reactant 2

HCID 159219132-Propoxybenzoyl chlorideHCID 178440442HCID 178440442, compound

Product 1

HCID 178458320HCID 178458320, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 2-n-propoxybenzoyl chloride (57.6 g, 0.291 mol) in dichloromethane (50 ml) was added dropwise to a stirred, ice-cooled suspension of 4-amino-3-propyl-1H-pyrazole-5-Carboxamide (the compound of Preparation 8 of WO 98/49166) (35.0 g, 0.208 mol) in dry pyridine (350 ml) and the resulting mixture stirred for 18 hours at room temperature, then evaporated under reduced pressure. The residue was azeotroped with toluene (2×100 ml) and the resulting brown solid triturated with ether (100 ml) to give the title compound (83.0 g) as a beige solid.

Workup

  1. temperaturecooled
  2. customevaporated under reduced pressure
  3. customThe residue was azeotroped with toluene (2×100 ml)
  4. customthe resulting brown solid triturated with ether (100 ml)

Sources & evidence

ORD record
ord-c792679185654b548d6641263d2c50f8
Source dataset
uspto-grants-2004_08
Patent number
US06784185B2

Reaction notes

Loading…