Triethylamine → HCID 86633685, compound

HRID 2265829Notes

Reaction equation

HRID 2265829 reaction equation
[OH:1][CH2:2][C:3]1([CH2:15][OH:16])[CH2:9][CH2:8][O:7][C:6]2[CH:10]=[CH:11][CH:12]=[CH:13][C:5]=2[C:4]1=[O:14].C(N(CC)CC)C.[F:24][C:25]1[CH:30]=[C:29]([F:31])[CH:28]=[CH:27][C:26]=1[N:32]=[C:33]=[S:34]>O1CCCC1>[OH:16][CH2:15][C:3]1([CH2:2][O:1][C:33](=[S:34])[NH:32][C:26]2[CH:27]=[CH:28][C:29]([F:31])=[CH:30][C:25]=2[F:24])[CH2:9][CH2:8][O:7][C:6]2[CH:10]=[CH:11][CH:12]=[CH:13][C:5]=2[C:4]1=[O:14]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 5188792,4-Difluoro-1-isothiocyanatobenzeneHCID 670731254,4-Bis(hydroxymethyl)-3,4-dihydro-2H-benzo[b]oxepin-5-one

Product 1

HCID 86633685HCID 86633685, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4,4-bis(hydroxymethyl)-3,4-dihydro-2H-benzo[b]oxepin-5-one (500 mg, 2.25 mmol) in 28 ml of tetrahydrofuran were added, at room temperature, triethylamine (0.34 ml, 2.48 mmol) and 2,4-difluorophenyl isothiocyanate (734 μl, 5.63 mmol). The mixture was heated to reflux for 72 hours, concentrated and purified by column chromatography on silica gel (eluent: 1:2 tert-butyl methyl ether/cyclohexane). The product was obtained in a yield of 376 mg (43%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 72 hours
  3. concentrationconcentrated
  4. custompurified by column chromatography on silica gel (eluent: 1:2 tert-butyl methyl ether/cyclohexane)
  5. customThe product was obtained in a yield of 376 mg (43%)

Sources & evidence

ORD record
ord-b427d66dc2b04007a93ebaba6595347e
Source dataset
uspto-grants-2010_12
Patent number
US07858613B2

Reaction notes

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