1,1'-Carbonyldiimidazole → HCID 477134, compound

HRID 440260Notes

Reaction equation

HRID 440260 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): δ3.16 (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-e214e7e5a2ed45adb3d8f6c8ca9e08ee
Source dataset
uspto-grants-1996_05
Patent number
US05519021

Reaction notes

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