Triphosgene → HCID 18442662, compound

HRID 458561Notes

Reaction equation

HRID 458561 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]([OH:17])([C:13]([F:16])([F:15])[F:14])[C:9]([F:12])([F:11])[F:10].Cl[C:19](Cl)([O:21]C(=O)OC(Cl)(Cl)Cl)Cl>C1COCC1>[F:16][C:13]([F:14])([F:15])[C:8]1([C:9]([F:10])([F:11])[F:12])[C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[NH:1][C:19](=[O:21])[O:17]1

Participants

4

Reactant 2

HCID 94429TriphosgeneHCID 27592682-(2-aminophenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol

Product 1

HCID 18442662HCID 18442662, compoundYield 60.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 2-(2-aminophenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol (4.20 g, 16.20 mmol) in THF (160 mL) was added triphosgene (4.80 g, 16.20 mmol). The reaction was stirred overnight, quenched with ammonium chloride solution (sat.) and extracted several times with ethyl acetate. The organic layer was dried over magnesium sulfate and triturated with ether/hexane to give 2.78 g of 4,4-bis(trifluoromethyl)-1,4-dihydro-2H-3,1-benzoxazin-2-one as a tan solid (60%). 1H NMR (DMSO-d6): δ 11.37 (s, 1H), 7.62 (m, 2H), 7.29 (t, J=7.5 Hz, 1H), 7.11 (dd, J=8.0, 0.8 Hz, 1H). MS (ESI) m/z 284 ([M−H]−); HRMS: calcd for C10H5F6NO2, 285.0224; found (ESI_FT), 286.0299; Anal. Calcd for C10H5F6NO2: C, 42.12; H, 1.77; N, 4.91. Found: C, 42.63; H, 1.79; N, 4.72.

Workup

  1. customquenched with ammonium chloride solution (sat.)
  2. extractionextracted several times with ethyl acetate
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. customtriturated with ether/hexane

Sources & evidence

ORD record
ord-951e52e08be64233a8691469274321b3
Source dataset
uspto-grants-2007_03
Patent number
US07192956B2

Reaction notes

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