Triethylamine → (2,4-Difluorophenyl)thiocarbamic acid O-(6-hydroxymethyl-5-oxo-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-ylmethyl)ester

HRID 2265830Notes

Reaction equation

HRID 2265830 reaction equation
[OH:1][CH2:2][C:3]1([CH2:15][OH:16])[CH2:9][CH2:8][CH2:7][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][CH2:7][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 670730866,6-Bis(hydroxymethyl)-6,7,8,9-tetrahydrobenzocyclohepten-5-one

Product 1

HCID 11964900(2,4-Difluorophenyl)thiocarbamic acid O-(6-hydroxymethyl-5-oxo-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-ylmethyl)ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6,6-bis(hydroxymethyl)-6,7,8,9-tetrahydrobenzocyclohepten-5-one (500 mg, 2.27 mmol) in 28 ml of tetrahydrofuran were added, at room temperature, triethylamine (0.35 ml, 2.50 mmol) and 2,4-difluorophenyl isothiocyanate (740 μl, 5.68 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 234 mg (26%).

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 234 mg (26%)

Sources & evidence

ORD record
ord-c87134869d694f10a3d7af0207b56e2a
Source dataset
uspto-grants-2010_12
Patent number
US07858613B2

Reaction notes

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