Dimethylformamide → HCID 57360982, compound

HRID 1766406Notes

Reaction equation

HRID 1766406 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:10]=[C:9](O)[N:8]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[Cl:18])[N:7]=1)=[O:5])[CH3:2].P(Br)(Br)([Br:21])=O.CN(C)[CH:26]=[O:27].ClCCl>ClCCCl>[CH2:1]([O:3][C:4]([C:6]1[C:10]([CH:26]=[O:27])=[C:9]([Br:21])[N:8]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[Cl:18])[N:7]=1)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6344DichloromethaneHCID 24613Phosphorus oxybromide2×HCID 178469350HCID 178469350, compound

Product 1

HCID 57360982HCID 57360982, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a stirred solution of 1-(2-chloro-phenyl)-5-hydroxy-1H-pyrazole-3-carboxylic acid ethyl ester I-1a (18.2 g) and phosphorus oxybromide (39 g) in 1,2-dichloroethane (200 ml) was added dimethylformamide (10.5 ml) over a 15-min period. The resulting mixture was heated at reflux for 3 hours, cooled, then an additional portion of phosphorus oxybromide (98 g) was added and refluxing was continued for 20 hours. The black reaction mixture was cooled, poured over ice (150 g) and stirred for 30 minutes. The mixture was extracted with dichloromethane (2×), the combined organic layers dried over magnesium sulfate and concentrated in vacuo to afford a dark oil. The oil was passed through a 200 g plug of silica gel, elueting with 30% hexanes:dichloromethane to afford the title compound I-1b as a yellow solid, 8.3 g.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux for 3 hours
  3. temperaturecooled
  4. temperaturerefluxing
  5. customThe black reaction mixture
  6. temperaturewas cooled
  7. extractionThe mixture was extracted with dichloromethane (2×)
  8. dry with materialthe combined organic layers dried over magnesium sulfate
  9. concentrationconcentrated in vacuo
  10. customto afford a dark oil

Sources & evidence

ORD record
ord-f32b3598691f4c0593e06836d662e578
Source dataset
uspto-grants-2007_06
Patent number
US07230024B2

Reaction notes

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