Formic Acid → 2-Chloropyrimidine-4-carboxamide

HRID 373587Notes

Reaction equation

HRID 373587 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8]#[N:9])[CH:5]=[CH:4][N:3]=1.Cl.C(O)=[O:12]>>[Cl:1][C:2]1[N:7]=[C:6]([C:8]([NH2:9])=[O:12])[CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 3

HCID 284Formic AcidHCID 313Hydrochloric AcidHCID 2466472-Chloropyrimidine-4-carbonitrile

Product 1

HCID 2470282-Chloropyrimidine-4-carboxamide

Procedure

338 g of 98% strength formic acid are introduced into a 1--1 round bottom flask fitted with magnetic stirring and containing 131.9 g (946 mmol) of 2-chloropyrimidine-4-carbonitrile, and a stream of gaseous hydrochloric acid is passed through slowly for 1 h 30 min. The mixture is allowed to stand overnight, the solid is isolated on sintered glass and is then purified by recrystallisation with filtration while hot, from a mixture of nitromethane and ethyl acetate. In this way, 107.03 g of grey solid are isolated as three crops, after drying under vacuum and with heating. Melting point: 152.5°-154° C.

Workup

  1. customfitted
  2. customthe solid is isolated on sintered glass
  3. filtrationis then purified by recrystallisation with filtration while hot,
  4. additionfrom a mixture of nitromethane and ethyl acetate

Sources & evidence

ORD record
ord-2cce353e70534a87bed4ad15e4cc0d60
Source dataset
uspto-grants-1992_11
Patent number
US05164397

Reaction notes

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