1,1'-Carbonyldiimidazole → HCID 477134, compound

HRID 2394246Notes

Reaction equation

HRID 2394246 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[C:9]([OH:16])([C:14]#[CH:15])[C:10]([F:13])([F:12])[F:11].[C:17](N1C=CN=C1)(N1C=CN=C1)=[O:18]>C1COCC1>[Cl:8][C:5]1[CH:6]=[CH:7][C:2]2[NH:1][C:17](=[O:18])[O:16][C:9]([C:14]#[CH:15])([C:10]([F:13])([F:11])[F:12])[C:3]=2[CH:4]=1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 18972706HCID 18972706, compound

Product 1

HCID 477134HCID 477134, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

A THF solution of 2-(2-amino-5-chlorophenyl)-1,1,1-trifluoro-3-butyn-2-ol (5.0 g, 20.0 mmol in 225 mL THF) was treated with 1,1'-carbonyldiimidazole (13.0 g, 80.0 mmol) and heated in an oil bath at 60° C. for 17 h. The THF was removed in vacuo, the residue dissolved in ethyl acetate then washed with 10% citric acid, sodium bicarbonate, water and brine before drying over sodium sulfate. Following filtration and evaporation in vacuo the crude product was isolated (3.6 g) and recrystallized from ethyl acetate:hexane. The product (+/-) 6-chloro-4-ethynyl-4-(1,1,1-trifluoromethyl)-1,4-dihydro-2H-3,1-benzoxazin-2-one was isolated as a white crystalline solid (3.22 g, 58.4% yield): mp 226°-227° C. 1H-NMR (CDCl3 +trace DMSO): δ 3.16 (s, 1H), 6.98 (d, J=3.3 Hz, 1H), 7.35 (m, 1H), 7.51 (s, 1H), 10.66 (s, 1H).

Workup

  1. customThe THF was removed in vacuo
  2. dissolutionthe residue dissolved in ethyl acetate
  3. washthen washed with 10% citric acid, sodium bicarbonate, water and brine
  4. dry with materialbefore drying over sodium sulfate
  5. filtrationfiltration and evaporation in vacuo the crude product
  6. customwas isolated (3.6 g)
  7. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-b08b01190de542cdbcb69fc1d73812a3
Source dataset
uspto-grants-1998_09
Patent number
US05811423

Reaction notes

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