Tetrahydrofuran → HCID 18376488, compound

HRID 2300691Notes

Reaction equation

HRID 2300691 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:30]3[CH:34]=[CH:33][N:32]=[C:31]3[CH3:35])[O:22][C:23]=2[CH2:24][CH2:25][CH2:26][C:27]([OH:29])=O)=[CH:15][CH:14]=1.[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:27](=[O:29])[CH2:26][CH2:25][CH2:24][C:23]1[O:22][C:21]([N:30]2[CH:34]=[CH:33][N:32]=[C:31]2[CH3:35])=[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 133692-ChloroethylamineHCID 11110750HCID 11110750, compound

Product 1

HCID 18376488HCID 18376488, compoundYield 85%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×HCID 8471TriethylamineSolvent

Procedure

Ethyl chloroformate (375 mg) was added dropwise to a tetrahydrofuran (20 ml)-N,N-dimethylformamide (10 ml) solution of 4-(4-chlorophenyl)-2-(2-methyl-1-imidazolyl)-5-oxazolebutanoic acid (1.00 g) and triethylamine at −30° C. After stirring for 30 minutes, the reaction mixture was added to the solution of 2-chloroethylamine (1.45 g) and N,N-dimethylformamide (20 ml) at 0° C. The resulting mixture was stirred for 1 hour at room temperature. Water was poured into the reaction mixture to give N-(2-chloroethyl)-4-(4-chlorophenyl)-2-(2-methyl-1-imidazolyl)-5-oxazolebutyramide (1.00 g, 85%). This was recrystallized from ethyl acetate-hexane to give colorless needles. mp 131-132° C.

Workup

  1. stirringThe resulting mixture was stirred for 1 hour at room temperature

Sources & evidence

ORD record
ord-d6d10463e6a2462c8edb0666ea4e965c
Source dataset
uspto-grants-2002_12
Patent number
US06498179B1

Reaction notes

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