Triethylamine → HCID 11964752, compound

HRID 2265821Notes

Reaction equation

HRID 2265821 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.[C:22]1([CH3:34])[CH:27]=[CH:26][C:25]([S:28]([N:31]=[C:32]=[O:33])(=[O:30])=[O:29])=[CH:24][CH:23]=1>O1CCCC1>[O:14]=[C:4]1[CH:3]([CH2:2][O:1][C:32](=[O:33])[NH:31][S:28]([C:25]2[CH:26]=[CH:27][C:22]([CH3:34])=[CH:23][CH:24]=2)(=[O:29])=[O:30])[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 77703p-Toluenesulfonyl isocyanateHCID 67073367HCID 67073367, compound

Product 1

HCID 11964752HCID 11964752, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-hydroxymethyl-3,4-dihydro-2H-benzo[b]thiepin-5-one (300 mg, 1.44 mmol) in 7 ml of tetrahydrofuran were added, at room temperature, triethylamine (0.22 ml, 1.6 mmol) and p-toluenesulfonyl isocyanate (312 mg, 1.586 mmol). The mixture was stirred at room temperature for 1.5 hours, concentrated and purified by column chromatography on silica gel (eluent: 1:9 tert.butyl methyl ether/dichloromethane). The product was obtained in a yield of 250 mg (43%).

Workup

  1. concentrationconcentrated
  2. custompurified by column chromatography on silica gel (eluent: 1:9 tert.butyl methyl ether/dichloromethane)
  3. customThe product was obtained in a yield of 250 mg (43%)

Sources & evidence

ORD record
ord-71fc4845194749f2afb1599b3438b024
Source dataset
uspto-grants-2010_12
Patent number
US07858613B2

Reaction notes

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