Tetrahydrofuran → HCID 18376445, compound

HRID 567178Notes

Reaction equation

HRID 567178 reaction equation
ClC(OCC)=O.O1CCCC1.[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[N:20]=[C:21]([N:29]3[CH:33]=[CH:32][N:31]=[C:30]3[CH3:34])[O:22][C:23]=2[CH2:24][CH2:25][C:26]([OH:28])=O)=[CH:15][CH:14]=1.Cl.[Cl:36][CH2:37][CH2:38][NH2:39]>O.CN(C)C=O.C(N(CC)CC)C>[Cl:36][CH2:37][CH2:38][NH:39][C:26](=[O:28])[CH2:25][CH2:24][C:23]1[O:22][C:21]([N:29]2[CH:33]=[CH:32][N:31]=[C:30]2[CH3:34])=[N:20][C:19]=1[C:16]1[CH:15]=[CH:14][C:13]([Cl:12])=[CH:18][CH:17]=1

Participants

8

Reactant 4

HCID 8028TetrahydrofuranHCID 10928Ethyl chloroformateHCID 97937372-Chloroethylamine hydrochlorideHCID 11034933HCID 11034933, compound

Product 1

HCID 18376445HCID 18376445, compoundYield 86%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent2×

Procedure

Ethyl chloroformate (590 mg) was dropwise added to a tetrahydrofuran (40 ml) solution of 4-(4-chlorophenyl)-2-(2-methyl-1-imidazolyl)-5-oxazolepropionic acid (1.50 g) and triethylamine (550 mg), at −30° C. After stirring for 30 minutes, the reaction mixture was poured into a solution as prepared from 2-chloroethylamine hydrochloride (2.62 g), triethylamine (2.29 g) and N,N-dimethylformamide (20 ml), at 0° C., and then stirred at room temperature for 1 hour. The reaction mixture was poured into water, and the crystals thus precipitated were collected by filtration to obtain N-(2-chloroethyl)-4-(4-chlorophenyl)-2-(2-methyl-1-imidazolyl)-5-oxazolepropionamide (1.53 g, 86%). This was recrystallized from ethyl acetate-hexane to give colorless needles. mp 155-156° C.

Workup

  1. additionthe reaction mixture was poured into a solution
  2. stirringstirred at room temperature for 1 hour
  3. customthe crystals thus precipitated
  4. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-833d1211028d43359fa8c89192ae205a
Source dataset
uspto-grants-2001_01
Patent number
US06177452B1

Reaction notes

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