Triethylamine → HCID 11964749, compound

HRID 2265819Notes

Reaction equation

HRID 2265819 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.[CH:22]1([N:28]=[C:29]=[O:30])[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1>O1CCCC1>[O:14]=[C:4]1[CH:3]([CH2:2][O:1][C:29](=[O:30])[NH:28][CH:22]2[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]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 18502Cyclohexyl isocyanateHCID 67073367HCID 67073367, compound

Product 1

HCID 11964749HCID 11964749, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 4-hydroxymethyl-3,4-dihydro-2H-benzo[b]thiepin-5-one (283 mg, 1.36 mmol) in 17 ml of tetrahydrofuran were added, at room temperature, triethylamine (0.21 ml, 1.5 mmol) and cyclohexyl isocyanate (682 μl, 5.56 mmol). The mixture was stirred at 80° C. for 24 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 190 mg (42%).

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 190 mg (42%)

Sources & evidence

ORD record
ord-3653c41d23ba48f4b5094ff03657feb3
Source dataset
uspto-grants-2010_12
Patent number
US07858613B2

Reaction notes

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