Triethylamine → HCID 18916426, compound

HRID 1290647Notes

Reaction equation

HRID 1290647 reaction equation
O=[C:2]1[NH:6][C:5]2[C:7]([Cl:25])=[CH:8][C:9]([F:24])=[C:10]([N:11]3[C:16](=[O:17])[CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[N:13]([CH3:22])[C:12]3=[O:23])[C:4]=2[O:3]1.P(Cl)(Cl)([Cl:28])=O.C(N(CC)CC)C>>[Cl:28][C:2]1[O:3][C:4]2[C:10]([N:11]3[C:16](=[O:17])[CH:15]=[C:14]([C:18]([F:20])([F:21])[F:19])[N:13]([CH3:22])[C:12]3=[O:23])=[C:9]([F:24])[CH:8]=[C:7]([Cl:25])[C:5]=2[N:6]=1

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 24813Phosphorus oxychlorideHCID 18916397HCID 18916397, compound

Product 1

HCID 18916426HCID 18916426, compound

Procedure

A stirring solution of 3.8 grams (10 mmole) of 3-(2-oxo-4-chloro-6-fluoro-2,3-dihydrobenzoxazol-7-yl)-1-methyl-6-trifluoromethyl-2,4-(1H,3H)pyrimidinedione and 7.7 grams (50 mmole) of phosphorus oxychloride is cooled in an ice bath. To this 5.0 grams (49.4 mmole) of triethylamine is added via syringe during a ten minute period. At the conclusion of this period the reaction mixture is heated to reflux where it stirs for four hours. After this period the reaction mixture is cooled to ambient temperature and poured into ice water. The resulting mixture is extracted with portions of diethyl ether. The extracts are combined, washed with an aqueous saturated sodium bicarbonate solution, dried with sodium sulfate, and filtered. The filtrate is concentrated under reduced pressure, yielding 3-(2,4-dichloro-6-fluorobenzoxazol-7-yl)-1-methyl-6-trifluoromethyl-2,4-(1H,3H)pyrimidinedione.

Workup

  1. temperatureAt the conclusion of this period the reaction mixture is heated
  2. temperatureto reflux where it
  3. extractionThe resulting mixture is extracted with portions of diethyl ether
  4. washwashed with an aqueous saturated sodium bicarbonate solution
  5. dry with materialdried with sodium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-9a83f534628f4ddbae5580fa6dd807fe
Source dataset
uspto-grants-1998_05
Patent number
US05753595

Reaction notes

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