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

HRID 866558ノート

反応式

HRID 866558 の反応式
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

参加物

9

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6569Methyl Ethyl Ketone溶媒

実験手順

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%

後処理

  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

出典と根拠

ORDレコード
ord-6ed1d37d9ea846dfb1e9c4e6c908e04e
出典データセット
uspto-grants-1978_07
特許番号
US04100168

反応ノート

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