Ammonia → HCID 14971802, compound

HRID 2082085Notes

Reaction equation

HRID 2082085 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]([CH2:18][C:19]([O:21]CC)=O)[O:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH3:24]>>[C:1]1([C:7]2[N:8]=[C:9]([CH2:18][C:19]([NH2:24])=[O:21])[O:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 2

HCID 222AmmoniaHCID 14971801HCID 14971801, compound

Product 1

HCID 14971802HCID 14971802, compoundYield 34%

Conditions

Temperature
130 °C

Procedure

A mixture of ethyl 4,5-diphenyl-2-oxazoleacetate (10.24 g, 33 mmol) and ammonia (35 mL) was heated in a bomb at about 130° C. for about 24 hours. After evaporation of the NH3, the residue was chromatographed on a column of silica gel using EtOAc/hexanes (4:1) as eluent to give the title compound (3.21 g, 34%), mp 129°-133° C. IR (KBr) 3340, 3200, 1665 cm-1 ; 1H NMR (CDCl3) δ3.83 (2H, s, CH2CONH2), 7.27 to 7.40 (6H, m, aromatic H), 6.50 to 6.68 (4H, m, aromatic H); MS m/z 279 (MH+).

Workup

  1. customAfter evaporation of the NH3
  2. customthe residue was chromatographed on a column of silica gel

Sources & evidence

ORD record
ord-c8818d2a5bd74714aa6b98094c5cc904
Source dataset
uspto-grants-1993_02
Patent number
US05187188

Reaction notes

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