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

HRID 1395467Notes

Reaction equation

HRID 1395467 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-4edfe7e2cbfd425f883b105bd6819834
Source dataset
uspto-grants-1980_05
Patent number
US04203994

Reaction notes

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