Triethylamine → HCID 11957765, compound

HRID 2265817Notes

Reaction equation

HRID 2265817 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.[Br:22][C:23]1[CH:28]=[CH:27][C:26]([N:29]=[C:30]=[O:31])=[CH:25][CH:24]=1>O1CCCC1>[O:14]=[C:4]1[CH:3]([CH2:2][O:1][C:30](=[O:31])[NH:29][C:26]2[CH:27]=[CH:28][C:23]([Br:22])=[CH:24][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 756094-Bromophenyl isocyanateHCID 67073367HCID 67073367, compound

Product 1

HCID 11957765HCID 11957765, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-hydroxymethyl-3,4-dihydro-2H-benzo[b]thiepin-5-one (224 mg, 1.08 mmol) in 14 ml of tetrahydrofuran were added, at room temperature, triethylamine (0.16 ml, 1.18 mmol) and 4-bromophenyl isocyanate (0.423 g, 2.15 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 250 mg (57%).

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 250 mg (57%)

Sources & evidence

ORD record
ord-142442afa7d9441389117ebc5d19602a
Source dataset
uspto-grants-2010_12
Patent number
US07858613B2

Reaction notes

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