Triethylamine → HCID 11964747, compound

HRID 2265816Notes

Reaction equation

HRID 2265816 reaction equation
[OH:1][CH2:2][CH:3]1[CH2:9][CH2:8][S: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:22][C:23]([F:34])([F:33])[C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([N:30]=[C:31]=[O:32])[CH:25]=1>O1CCCC1>[O:14]=[C:4]1[CH:3]([CH2:2][O:1][C:31](=[O:32])[NH:30][C:26]2[CH:27]=[CH:28][CH:29]=[C:24]([C:23]([F:22])([F:34])[F:33])[CH:25]=2)[CH2:9][CH2:8][S:7][C:6]2[CH:10]=[CH:11][CH:12]=[CH:13][C:5]1=2

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 94833-(Trifluoromethyl)phenyl isocyanateHCID 67073367HCID 67073367, compound

Product 1

HCID 11964747HCID 11964747, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-hydroxymethyl-3,4-dihydro-2H-benzo[b]thiepin-5-one (256 mg, 1.23 mmol) in 15 ml of tetrahydrofuran were added, at room temperature, triethylamine (0.19 ml, 1.4 mmol) and α,α,α-trifluoro-m-tolyl isocyanate (345 μl, 2.46 mmol). The mixture was stirred at room temperature for 2 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 180 mg (37%).

Workup

  1. concentrationconcentrated
  2. custompurified by column chromatography on silica gel (eluent: 1:2 tert-butyl methyl ether/cyclohexane)
  3. customThe product was obtained in a yield of 180 mg (37%)

Sources & evidence

ORD record
ord-d86c210558a54b459ea274039a384a1f
Source dataset
uspto-grants-2010_12
Patent number
US07858613B2

Reaction notes

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