Tetrahydrofuran → HCID 477123, compound

HRID 2394245Notes

Reaction equation

HRID 2394245 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[C:9]([OH:18])([CH2:14][CH2:15][CH:16]=[CH2:17])[C:10]([F:13])([F:12])[F:11].[C:19](N1C=CN=C1)(N1C=CN=C1)=[O:20].C1COCC1>CCOC(C)=O>[F:12][C:10]([C:9]1([CH2:14][CH2:15][CH:16]=[CH2:17])[C:3]2[CH:4]=[C:5]([Cl:8])[CH:6]=[CH:7][C:2]=2[NH:1][C:19](=[O:20])[O:18]1)([F:13])[F:11]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 682631,1'-CarbonyldiimidazoleHCID 15817164HCID 15817164, compound

Product 1

HCID 477123HCID 477123, compoundYield 61.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To a 200 mL round bottomed flask with a stirring bar, argon inlet and a reflux condenser was added (+/-) 2-(2-Amino-5-chlorophenyl)-1,1,1-trifluoro-5-hexen-2-ol (4.80 g, 17.16 mmol), 1,1'-carbonyldiimidazole (13.91 g, 85.81 mmol) and dry THF (75 mL). This mixture was heated at 60° C. for 18 h. The cooled reaction mixture was diluted with EtOAc and washed with H2O (3×200 mL) and brine (250 mL). Drying (MgSO4), filtration, removal of the solvent in vacuo, followed by recrystallization from boiling EtOAc-hexane gave 3.22 g of (+/-) 4-(1,1,1,-trifluoromethyl)-4(1-buten-4-yl)-6-chloro-1,4-dihydro-2H-3,1-benzoxazin-2-one as a white crystalline solid, mp: 165°-166° C. 1H NMR (CDCl3): δ 1.99 (m, 1H), 2.09-2.40 (m, 3H), 5.00 (d, 1H, J=1.4 Hz), 5.03 (dd, 1H, J=1.4, 7.9), 5.78 (m, 1H), 6.85 (d, 1H, J=8.6 Hz), 7.21 (br s, 1H), 7.35 (dd, 1H, J=2.2, 8.6 Hz), 9.63 (br s, 1H).

Workup

  1. customThe cooled reaction mixture
  2. washwashed with H2O (3×200 mL) and brine (250 mL)
  3. customDrying
  4. filtration(MgSO4), filtration, removal of the solvent in vacuo
  5. customfollowed by recrystallization

Sources & evidence

ORD record
ord-c738cb42573540469234a944b99107c2
Source dataset
uspto-grants-1998_09
Patent number
US05811423

Reaction notes

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