Diethylamine → Ethyl 2-(diethylamino)-4-trifluoromethyl-5-oxazolecarboxylate

HRID 359264Notes

Reaction equation

HRID 359264 reaction equation
Cl[C:2]1[O:3][C:4]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:5]([C:7]([F:10])([F:9])[F:8])[N:6]=1.[CH2:16]([NH:18][CH2:19][CH3:20])[CH3:17]>C1(C)C=CC=CC=1>[CH2:16]([N:18]([CH2:19][CH3:20])[C:2]1[O:3][C:4]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:5]([C:7]([F:10])([F:9])[F:8])[N:6]=1)[CH3:17]

Participants

4

Reactant 2

HCID 8021DiethylamineHCID 12785855Ethyl 2-chloro-4-(trifluoromethyl)oxazole-5-carboxylate

Product 1

HCID 20064751Ethyl 2-(diethylamino)-4-trifluoromethyl-5-oxazolecarboxylateYield 90.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a reaction vessel containing a stirred mixture of 3.15 g (13 mmol) of ethyl 2-chloro-4-trifluoromethyl-5-oxazolecarboxylate in 25 ml of toluene, there was added 3 ml (29 mmol) of diethylamine. The reactionmixture was stirred at ambient temperature for 4 hours and then suction filtered. The filtrate was washed with 5% hydrochloric acid, then with saturated brine, then dried over sodium sulfate and concentrated under reduced pressure to yield 3.3 g of a pale yellow oil. This oil was subjected to Kugelrohr distillation (60° C. @ 3 mm Hg) to remove trace amounts of starting material. Further Kugelrohr distillation provided 2.9 g of colorless oil (b.p. 110° C. @ 3 mm Hg) identified in Table I.

Workup

  1. additionTo a reaction vessel containing
  2. filtrationsuction filtered
  3. washThe filtrate was washed with 5% hydrochloric acid
  4. dry with materialwith saturated brine, then dried over sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e6fe2690338c45269875b4c6c65559df
Source dataset
uspto-grants-1991_03
Patent number
US05000775

Reaction notes

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