Water → HCID 67768315, compound

HRID 1720217Notes

Reaction equation

HRID 1720217 reaction equation
[Na+:1].[NH:2]1[CH:6]=[CH:5][C:4]([C:7]2[N:15]=[CH:14][CH:13]=[CH:12][C:8]=2[C:9]([O-:11])=[O:10])=[N:3]1.[F:16][C:17]1[CH:18]=[C:19]([N:24]=[C:25]=[O:26])[CH:20]=[C:21]([F:23])[CH:22]=1.[N-]=C=O.O>CN(C=O)C>[Na+:1].[F:16][C:17]1[CH:18]=[C:19]([NH:24][C:25]([N:2]2[CH:6]=[CH:5][C:4]([C:7]3[N:15]=[CH:14][CH:13]=[CH:12][C:8]=3[C:9]([O-:11])=[O:10])=[N:3]2)=[O:26])[CH:20]=[C:21]([F:23])[CH:22]=1

Participants

6

Reactant 4

HCID 962WaterHCID 105034IsocyanateHCID 27792821,3-Difluoro-5-isocyanatobenzeneHCID 178524452HCID 178524452, compound

Product 1

HCID 67768315HCID 67768315, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

0.95 g (4.5 mM) of 2-(pyrazol-3-yl)-nicotinic acid sodium salt are stirred in 20 ml of DMF and 0.7 g (4.5 mM) of 3,5-difluorophenyl isocyanate added. After stirring for 1 hr at RT, a further 0.21 g of isocyanate in DMF are added. The DMF is stripped-off on a Kugelrohr and the resulting solid stirred with 4 ml water and filtered. The filtrate is chromatographed on a reverse phase column with 100 ml of water followed by 100 ml water-methanol. The product containing fraction was lypholized to yield the title product m.p. 165°-170° C.

Workup

  1. filtrationfiltered
  2. customThe filtrate is chromatographed on a reverse phase column with 100 ml of water
  3. additionThe product containing fraction

Sources & evidence

ORD record
ord-329a30f61a924d089b9439e48379b65d
Source dataset
uspto-grants-1996_04
Patent number
US05506191

Reaction notes

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