Formamidine acetate → 5-Chloropyrimidine-4-carboxylic acid

HRID 614379ノート

反応式

HRID 614379 の反応式
C[O-].[Na+].[C:4]([OH:12])(=[O:11])/[C:5](=[C:7](\[CH:9]=O)/[Cl:8])/Cl.C(O)(=O)C.[CH:17]([NH2:19])=[NH:18]>CO>[C:4]([C:5]1[C:7]([Cl:8])=[CH:9][N:19]=[CH:17][N:18]=1)([OH:12])=[O:11]

参加物

5

反応物 3

HCID 160693Formamidine acetateHCID 2771871Mucochloric AcidHCID 10942334Sodium Methoxide

生成物 1

HCID 200293965-Chloropyrimidine-4-carboxylic acid収率 35.1%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

Sodium methoxide (162 g) is added to a solution of mucochloric acid (169 g) and formamidine acetate (208 g) in methanol (3 liters) over the course of 20 minutes, and the reaction mixture is heated for 1 hour at 35°-40° C., and then for one and a half hours under reflux. The solvent is removed and water (500 cc) is added to the residue. The aqueous mixture is extracted with ethyl acetate (2 liters). The aqueous phase is brought to pH 1 by the addition of concentrated hydrochloric acid, and the aqueous phase is extracted with ethyl acetate (5 liters). The organic phase is dried over anhydrous magnesium sulphate, filtered and then concentrated to dryness. The residue is washed with diethyl ether (300 cc) and then with diisopropyl ether (600 cc). 4-Carboxy-5-chloropyrimidine (55.6 g), melting at 190° C., is obtained.

後処理

  1. temperaturethe reaction mixture is heated for 1 hour at 35°-40° C.
  2. temperaturefor one and a half hours under reflux
  3. customThe solvent is removed
  4. additionwater (500 cc) is added to the residue
  5. extractionThe aqueous mixture is extracted with ethyl acetate (2 liters)
  6. additionThe aqueous phase is brought to pH 1 by the addition of concentrated hydrochloric acid
  7. extractionthe aqueous phase is extracted with ethyl acetate (5 liters)
  8. dry with materialThe organic phase is dried over anhydrous magnesium sulphate
  9. filtrationfiltered
  10. concentrationconcentrated to dryness
  11. washThe residue is washed with diethyl ether (300 cc)

出典と根拠

ORDレコード
ord-3a46c32cb00c48b088a319e662afffb7
出典データセット
uspto-grants-1979_03
特許番号
US04144339

反応ノート

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