Eclazolast → 5-Chloro-N-(2-ethoxyethyl)-1,3-benzoxazole-2-carboxamide

HRID 1154521Notes

Reaction equation

HRID 1154521 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([C:10]([O:12]CCOCC)=O)=[N:7][C:6]=2[CH:18]=1.[CH2:19]([O:21][CH2:22][CH2:23][NH2:24])[CH3:20]>C1COCC1>[CH2:19]([O:21][CH2:22][CH2:23][NH:24][C:10]([C:8]1[O:9][C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:18][C:6]=2[N:7]=1)=[O:12])[CH3:20]

Participants

4

Reactant 2

HCID 54550EclazolastHCID 66970Ethoxyethylamine

Product 1

HCID 133855535-Chloro-N-(2-ethoxyethyl)-1,3-benzoxazole-2-carboxamideYield 90.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-ethoxyethyl 5-chlorobenzoxazol-2-carboxylate (10 g) and 3.5 g of ethoxyethylamine in 10 ml of THF was stirred at room temperature for 2 hours. The precipitated product was filtered and washed well with hexane to give 9 g of product; mp 110°-111° C.

Workup

  1. filtrationThe precipitated product was filtered
  2. washwashed well with hexane

Sources & evidence

ORD record
ord-e4ad9de29a11461c9ba5b669f4a581a9
Source dataset
uspto-grants-1984_12
Patent number
US04490373

Reaction notes

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