Ethanolamine → 2-[(1,1-dimethylethyl)amino]-N-(2-hydroxyethyl)-4-(trifluoromethyl)-5-oxazolecarboxamide

HRID 359291Notes

Reaction equation

HRID 359291 reaction equation
[CH2:1]([CH2:3][NH2:4])[OH:2].C(N(CC)CC)C.[C:12]([NH:16][C:17]1[O:18][C:19]([C:26](Cl)=[O:27])=[C:20]([C:22]([F:25])([F:24])[F:23])[N:21]=1)([CH3:15])([CH3:14])[CH3:13]>C(Cl)Cl>[CH3:13][C:12]([NH:16][C:17]1[O:18][C:19]([C:26]([NH:4][CH2:3][CH2:1][OH:2])=[O:27])=[C:20]([C:22]([F:25])([F:24])[F:23])[N:21]=1)([CH3:15])[CH3:14]

Participants

5

Reactant 3

HCID 700EthanolamineHCID 8471TriethylamineHCID 20064749HCID 20064749, compound

Product 1

HCID 200647382-[(1,1-dimethylethyl)amino]-N-(2-hydroxyethyl)-4-(trifluoromethyl)-5-oxazolecarboxamideYield 34.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

By the procedure of Example 38, a stirred mixture of 50 ml methylene chloride, 0.70 g (11.46 mmol) of ethanolamine, 1.27 g (12.61 mmol) of triethylamine, and 3.1 g (11.46 mmol) of 2-(tert-butylamino)-4-trifluoromethyl-5-oxazolecarbonyl chloride, was reacted for 64 hours at ambient temperature. The product was separated and then recrystallized to yield 1.16 g of a yellow solid product (m.p.=154°-156° C.) identified in Table 1.

Workup

  1. customwas reacted for 64 hours at ambient temperature
  2. customThe product was separated
  3. customrecrystallized

Sources & evidence

ORD record
ord-aa8efeaa3af94585af5405daee51a159
Source dataset
uspto-grants-1991_03
Patent number
US05000775

Reaction notes

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