Ethyl Acetate → HCID 22021890, compound

HRID 2099185Notes

Reaction equation

HRID 2099185 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-fe4e2d4500c540c7a919ee9e335eb350
Source dataset
uspto-grants-2009_08
Patent number
US07569564B2

Reaction notes

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