Methyl chloroformate → Benzoic Acid

HRID 2051608노트

반응식

HRID 2051608 반응식
COC(Cl)=O.C(O[C:11]1N=[C:18]([CH3:20])[C:17](Cl)=[CH:16][C:12]=1[C:13]([OH:15])=[O:14])CCC.NCCC1C=CC(C(O)=O)=CC=1.[Na].C([O-])(=O)C.[Na+]>CC(C)=O.C(N(CC)CC)C>[C:13]([OH:15])(=[O:14])[C:12]1[CH:11]=[CH:20][CH:18]=[CH:17][CH:16]=1

참가 물질

7

반응물 4

HCID 6586Methyl chloroformateHCID 517045Sodium AcetateHCID 203792372-Butoxy-5-chloro-6-methyl-nicotinic acidHCID 705908304-(2-Aminoethyl)-benzoic acid sodium

생성물 1

HCID 243Benzoic Acid

시약·촉매·용매 2

HCID 180Acetone용매2회HCID 8471Triethylamine용매

실험 절차

2.8 g of triethylamine and 2.6 g of chloroformic acid methyl ester are added, while stirring and cooling with ice, to 6.1 g of 2-butoxy-5-chloro-6-methyl-nicotinic acid (melting point 95°-97° C., prepared by chlorinating 2-butoxy-6-methyl-nicotinic acid in dilute glacial acetic acid) in 75 ml of acetone. The mixture is stirred for a further 15 minutes and then added, while stirring, to 25 ml of a 1-molar solution of 4-(2-amino-ethyl)-benzoic acid-sodium, additionally containing 0.025 mol of sodium acetate and to which 25 ml of acetone has been added. Stirring of the mixture is continued for 2 hours at room temperature, the acetone is removed under reduced pressure, the remaining aqueous solution is acidified, the precipitated reaction product is filtered off with suction, reprecipitated from ammonia and recrystallized from dilute methanol or ethyl acetate. The 4-(2-<2-butoxy-5-chloro-6-methyl-nicotinamido>-ethyl)-benzoic acid obtained melts at 148°-150° C.

후처리

  1. stirringThe mixture is stirred for a further 15 minutes
  2. additionadded
  3. stirringStirring of the mixture
  4. customthe acetone is removed under reduced pressure
  5. customthe precipitated reaction product
  6. filtrationis filtered off with suction
  7. customreprecipitated from ammonia
  8. customrecrystallized from dilute methanol or ethyl acetate

출처 및 근거

ORD 기록
ord-cce071f07ec347b98dd8c54d8dd9d893
출처 데이터셋
uspto-grants-1980_01
특허 번호
US04181658

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