Ethyl Acetate → HCID 22021890, compound

HRID 1258076Notes

Reaction equation

HRID 1258076 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([F:14])[CH:9]=2)=[CH:4][C:3]=1[CH:15]([OH:17])[CH3:16].Cl[C:19](Cl)([O:21]C(=O)OC(Cl)(Cl)Cl)Cl.C(=O)(O)[O-].[Na+].C(OCC)(=O)C>C1COCC1>[F:14][C:10]1[CH:9]=[C:8]([C:5]2[CH:6]=[CH:7][C:2]3[NH:1][C:19](=[O:21])[O:17][CH:15]([CH3:16])[C:3]=3[CH:4]=2)[CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 94429TriphosgeneHCID 516892Sodium BicarbonateHCID 220218991-(4-Amino-3'-fluoro[1,1'-biphenyl]-3-yl)ethanol

Product 1

HCID 22021890HCID 22021890, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of the above alcohol (0.2 g, 0.87 mmol) and triphosgene in anhydrous THF (20 mL) was stirred at room temperature under nitrogen. After 15 minutes, the mixture was treated with a saturated aqueous sodium bicarbonate solution (30 mL) and ethyl acetate (40 mL). The organic layer was separated, dried (MgSO4), and evaporated to give 6-(3-fluorophenyl)-4-methyl-1,4-dihydro-2H-3,1-benzoxazin-2-one as a white solid (0.18 g, 81%): mp 160-161° C.; 1H-NMR (DMSO-d6) δ 10.31 (s, 1H), 7.62 (dd, 1H, J=8.2, 1.9 Hz), 7.57 (s, 1H), 7.44-7.53 (m, 3H), 7.13-7.20 (m 1H), 6.97 (d, 1H, J=8.2 Hz), 5.57 (q, 1H, J=6.6 Hz), 1.63 (d, 3H, J=6.6 Hz). MS (ESI) m/z 256 [M−H]−.

Workup

  1. customThe organic layer was separated
  2. dry with materialdried (MgSO4)
  3. customevaporated

Sources & evidence

ORD record
ord-5082afbf1a15414c818d55f88cb57a88
Source dataset
uspto-grants-2013_06
Patent number
US08466146B2

Reaction notes

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