Ethyl chloroformate → [(3-Phenyl-5-isoxazolyl)methyl]carbamic acid, ethyl ester

HRID 2420124Notes

Reaction equation

HRID 2420124 reaction equation
[NH2:1][CH2:2][C:3]1[O:7][N:6]=[C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:4]=1.Cl[C:15]([O:17][CH2:18][CH3:19])=[O:16]>N1C=CC=CC=1>[C:8]1([C:5]2[CH:4]=[C:3]([CH2:2][NH:1][C:15](=[O:16])[O:17][CH2:18][CH3:19])[O:7][N:6]=2)[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 10928Ethyl chloroformateHCID 27641651-(3-Phenyl-1,2-oxazol-5-yl)methanamine

Product 1

HCID 60025831[(3-Phenyl-5-isoxazolyl)methyl]carbamic acid, ethyl ester

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A 7 g. portion of the product of Example 8 was dissolved in 50 ml. of pyridine, cooled in an ice bath, and combined with 10 ml. of ethyl chloroformate. The mixture was stirred at ice bath temperature for 1 hour and allowed to warm to room temperature while being stirred for 2 hours more. The mixture was then poured into ice water and the crude product was separated by filtration and purified by chromatography over silica gel with ethyl acetate as the eluent. The yield was 6 g. of purified [(3-phenyl-5-isoxazolyl)-methyl]carbamic acid, ethyl ester, m.p. 82°.

Workup

  1. stirringwhile being stirred for 2 hours more
  2. customthe crude product was separated by filtration
  3. custompurified by chromatography over silica gel with ethyl acetate as the eluent

Sources & evidence

ORD record
ord-9d17f9327255462783cd98d3afa59506
Source dataset
uspto-grants-1978_08
Patent number
US04109002

Reaction notes

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