Ammonia → HCID 53894997, compound

HRID 2300686Notes

Reaction equation

HRID 2300686 reaction equation
ClC(OCC)=O.[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[N:15]=[C:16]([N:24]3[CH:28]=[CH:27][N:26]=[C:25]3[CH3:29])[O:17][C:18]=2[CH2:19][CH2:20][C:21](O)=[O:22])=[CH:10][CH:9]=1.[NH3:30]>O.O1CCCC1.C(N(CC)CC)C>[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[N:15]=[C:16]([N:24]3[CH:28]=[CH:27][N:26]=[C:25]3[CH3:29])[O:17][C:18]=2[CH2:19][CH2:20][C:21]([NH2:30])=[O:22])=[CH:10][CH:9]=1

Participants

7

Reactant 3

HCID 222AmmoniaHCID 10928Ethyl chloroformateHCID 11034933HCID 11034933, compound

Product 1

HCID 53894997HCID 53894997, compoundYield 90%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8471TriethylamineSolvent

Procedure

Ethyl chloroformate (395 mg) was dropwise added to a tetrahydrofuran (40 ml) solution of 4-(4-chlorophenyl)-2-(2-methyl-1-imidazolyl)-5-oxazolepropionic acid (1.00 g) and triethylamine (365 mg), at +30° C. After stirring for 40 minutes, the reaction mixture was added to a mixture of aqueous ammonia (28%, 30 ml) and tetrahydrofuran (10 ml) at 0° C., and then stirred at room temperature for 1 hour. Water was added to the reaction mixture, and the crystals thus precipitated were collected by filtration to obtain 4-(4-chlorophenyl)-2-(2-methyl-1-imidazolyl)-5-oxazolepropionamide (900 mg, 90%). This was recrystallized from methanol-ethyl acetate to give colorless needles. mp 215-216° C.

Workup

  1. stirringstirred at room temperature for 1 hour
  2. customthe crystals thus precipitated
  3. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-e671033a869e42de9d02e0806f113b38
Source dataset
uspto-grants-2002_12
Patent number
US06498179B1

Reaction notes

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