2-(dimethylamino)-4-(trifluoromethyl)-6H-1,3-oxazin-6-one → HCID 22614259, compound

HRID 842545Notes

Reaction equation

HRID 842545 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][N:6]2[NH2:11].CN(C)[C:14]1[O:15][C:16](=[O:24])[CH:17]=[C:18]([C:20]([F:23])([F:22])[F:21])[N:19]=1>C(O)(=O)C>[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][N:6]2[N:11]1[C:16](=[O:24])[CH:17]=[C:18]([C:20]([F:23])([F:22])[F:21])[NH:19][C:14]1=[O:15]

Participants

4

Reactant 2

HCID 37238622-(dimethylamino)-4-(trifluoromethyl)-6H-1,3-oxazin-6-oneHCID 22614254HCID 22614254, compound

Product 1

HCID 22614259HCID 22614259, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

A mixture of 169A, glacial acetic acid (30 mL) and 2-dimethylamino-4-trifluoromethyl-[1,3]oxazin-6-one (2.76 g, 13.3 mmol) is stirred for 4.5 h under reflux, whereupon the acetic acid was removed in vacuo. The residue is diluted with ethyl acetate, washed with water and subsequently dried over sodium sulfate. The crude product (3 g) is obtained after removal of the drying agent by filtration and evaporation of the solvent. The product (0.88 g) is obtained as a brown oil after flash chromatography (ethyl acetate/petrol ether 2/8).

Workup

  1. customwas removed in vacuo
  2. additionThe residue is diluted with ethyl acetate
  3. washwashed with water
  4. dry with materialsubsequently dried over sodium sulfate
  5. customThe crude product (3 g) is obtained
  6. customafter removal of the drying agent
  7. filtrationby filtration and evaporation of the solvent

Sources & evidence

ORD record
ord-ed6773e6ace1483499058d24eb8ddf19
Source dataset
uspto-grants-2002_04
Patent number
US06376426B1

Reaction notes

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