Sodium Cyanide → 2-[2-(4-Chloroanilino)-5-benzoxazolyl]propionic acid

HRID 866558노트

반응식

HRID 866558 반응식
C[N:2]([C:11]1[O:12][C:13]2[CH:19]=[CH:18][C:17]([CH:20]([CH3:24])[C:21]([OH:23])=[O:22])=[CH:16][C:14]=2[N:15]=1)[C:3]1[CH:8]=[CH:7][C:6]([Cl:9])=[C:5](Cl)[CH:4]=1.COC1C=CC(NC2OC3C=C(C(C)C#N)C=CC=3N=2)=CC=1.ClC1C=CC(NC2OC3C=CC(C(C)C(OCC)=O)=CC=3N=2)=CC=1.[I-].[Li+].[C-]#N.[Na+].C(=O)(O)[O-].[Na+]>O.C(C(C)=O)C>[Cl:9][C:6]1[CH:5]=[CH:4][C:3]([NH:2][C:11]2[O:12][C:13]3[CH:19]=[CH:18][C:17]([CH:20]([CH3:24])[C:21]([OH:23])=[O:22])=[CH:16][C:14]=3[N:15]=2)=[CH:8][CH:7]=1

참가 물질

9

반응물 6

HCID 8929Sodium CyanideHCID 66321Lithium iodideHCID 516892Sodium BicarbonateHCID 203195952-[2-(4-Methoxyanilino)-6-benzoxazolyl]propionitrileHCID 20319622Ethyl 2-[2-(4-chloroanilino)-5-benzoxazolyl]propionateHCID 203196342-[2-(N-methyl-3,4-dichloroanilino)-5-benzoxazolyl]propionic acid

생성물 1

HCID 203196432-[2-(4-Chloroanilino)-5-benzoxazolyl]propionic acid

시약·촉매·용매 2

HCID 962Water용매HCID 6569Methyl Ethyl Ketone용매

실험 절차

2-[2-(N-methyl-3,4-dichloroanilino)-5-benzoxazolyl]propionic acid (h) 2-[2-(4-methoxyanilino)-6-benzoxazolyl]propionic acid. Production of the acids was confirmed by thin-layer chromatography. (i) A stirred mixture of ethyl 2-[2-(4-chloroanilino)-5-benzoxazolyl]propionate (2.9g.), dry lithium iodide (10g.), sodium cyanide (0.4g.) and methyl ethyl ketone (35 ml.) was heated under reflux for 18 hours. The solution was diluted with water and made alkaline with sodium bicarbonate. The solution was washed several times with chloroform, filtered through a `Supercel` pad and acidified with concentrated hydrochloric acid. The solid obtained was filtered off, washed with water and recrystallised from aqueous methanol to give 2-[2-(4-chloroanilino)-5-benzoxazolyl]propionic acid as a buff powder, mpt 206°-8° C, which was characterised by ir, uv and NMR spectroscopy and by micro analysis which gave: C 60.45% H 4.31% N 8.75%. C16H13ClN2O3 requires C 60.66% H 4.11% N 8.85%

후처리

  1. temperaturewas heated
  2. temperatureunder reflux for 18 hours
  3. washThe solution was washed several times with chloroform
  4. filtrationfiltered through a `Supercel` pad
  5. customThe solid obtained
  6. filtrationwas filtered off
  7. washwashed with water
  8. customrecrystallised from aqueous methanol

출처 및 근거

ORD 기록
ord-6ed1d37d9ea846dfb1e9c4e6c908e04e
출처 데이터셋
uspto-grants-1978_07
특허 번호
US04100168

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