Triethylamine → (3-Trifluoromethylphenyl)thiocarbamic acid O-(6-hydroxymethyl-5-oxo-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-ylmethyl)ester

HRID 2265828Notes

Reaction equation

HRID 2265828 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]([F:36])([F:35])[C:26]1[CH:27]=[C:28]([N:32]=[C:33]=[S:34])[CH:29]=[CH:30][CH:31]=1>O1CCCC1>[OH:16][CH2:15][C:3]1([CH2:2][O:1][C:33](=[S:34])[NH:32][C:28]2[CH:29]=[CH:30][CH:31]=[C:26]([C:25]([F:24])([F:35])[F:36])[CH:27]=2)[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 1372321-Isothiocyanato-3-(trifluoromethyl)benzeneHCID 670730866,6-Bis(hydroxymethyl)-6,7,8,9-tetrahydrobenzocyclohepten-5-one

Product 1

HCID 11964898(3-Trifluoromethylphenyl)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, 2.5 mmol) and 3-(trifluoromethyl)phenyl isothiocyanate (862 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 ethyl acetate/hexane). The product was obtained in a yield of 284 mg (30%).

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 ethyl acetate/hexane)
  5. customThe product was obtained in a yield of 284 mg (30%)

Sources & evidence

ORD record
ord-6bcd2610b50d46b9b5e68dd58e68b67b
Source dataset
uspto-grants-2010_12
Patent number
US07858613B2

Reaction notes

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