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

HRID 866558Notes

Reaction equation

HRID 866558 reaction equation
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

Participants

9

Reactant 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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6569Methyl Ethyl KetoneSolvent

Procedure

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%

Workup

  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

Sources & evidence

ORD record
ord-6ed1d37d9ea846dfb1e9c4e6c908e04e
Source dataset
uspto-grants-1978_07
Patent number
US04100168

Reaction notes

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