Oxalyl chloride → HCID 86667940, compound

HRID 403529Notes

Reaction equation

HRID 403529 reaction equation
[F:1][C:2]1[CH:22]=[CH:21][CH:20]=[CH:19][C:3]=1[CH2:4][N:5]1[C:9]([C:10]([NH2:12])=[O:11])=[CH:8][C:7]([C:13]2[N:18]=[CH:17][CH:16]=[CH:15][N:14]=2)=[N:6]1.C(Cl)(=O)[C:24](Cl)=[O:25]>ClCCCl>[F:1][C:2]1[CH:22]=[CH:21][CH:20]=[CH:19][C:3]=1[CH2:4][N:5]1[C:9]([C:10]([N:12]=[C:24]=[O:25])=[O:11])=[CH:8][C:7]([C:13]2[N:18]=[CH:17][CH:16]=[CH:15][N:14]=2)=[N:6]1

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 66633948HCID 66633948, compound

Product 1

HCID 86667940HCID 86667940, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A mixture of 1-(2-fluorobenzyl)-3-(pyrimidin-2-yl)-1H-pyrazole-5-carboxamide (120 mg, 1 equiv) and oxalyl chloride (106 μl, 3 equiv) in 1,2-dichloroethane (2.0 ml) was heated to reflux for 24 h. The mixture was cooled to room temperature and purified by column chromatography (0 to 100% ethyl acetate in hexanes) to give 68 mg of 1-(2-fluorobenzyl)-3-(pyrimidin-2-yl)-1H-pyrazole-5-carbonyl isocyanate (52% yield) as a brown solid.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 24 h
  3. custompurified by column chromatography (0 to 100% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-84939f9b6f1e49b2b0961d80a79924b2
Source dataset
uspto-grants-2014_06
Patent number
US08748442B2

Reaction notes

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