Phenyl isocyanate → HCID 67072887, compound

HRID 2265815Notes

Reaction equation

HRID 2265815 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([N:28]=[C:29]=[O:30])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>O1CCCC1>[O:14]=[C:4]1[CH:3]([CH2:2][O:1][C:29](=[O:30])[NH:28][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH: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 7672Phenyl isocyanateHCID 8471TriethylamineHCID 67073367HCID 67073367, compound

Product 1

HCID 67072887HCID 67072887, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-hydroxymethyl-3,4-dihydro-2H-benzo[b]thiepin-5-one (359 mg, 1.726 mmol) in 22 ml of tetrahydrofuran were added, at 0° C., triethylamine (0.26 ml, 1.9 mmol) and phenyl isocyanate (410 μl, 3.8 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 350 mg (62%).

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 350 mg (62%)

Sources & evidence

ORD record
ord-d16a0c06d5f845e9ae3012807b7d8fd0
Source dataset
uspto-grants-2010_12
Patent number
US07858613B2

Reaction notes

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