Triethylamine → HCID 11964745, compound

HRID 2265814Notes

Reaction equation

HRID 2265814 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.[CH2:22]([N:27]=[C:28]=[O:29])[CH2:23][CH2:24][CH2:25][CH3:26]>O1CCCC1>[O:14]=[C:4]1[CH:3]([CH2:2][O:1][C:28](=[O:29])[NH:27][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[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 206036Pentane, 1-isocyanato-HCID 67073367HCID 67073367, compound

Product 1

HCID 11964745HCID 11964745, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-hydroxymethyl-3,4-dihydro-2H-benzo[b]thiepin-5-one (264 mg, 1.27 mmol) in 16 ml of tetrahydrofuran were added, at 0° C., triethylamine (0.2 ml, 1.4 mmol) and n-pentyl isocyanate (492 μl, 4.9 mmol). The mixture was heated under reflux for 15 hours, concentrated and purified by column chromatography on silica gel (eluent: 4:1 diisopropyl ether/hexane). The product was obtained in a yield of 145 mg (35%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 15 hours
  3. concentrationconcentrated
  4. custompurified by column chromatography on silica gel (eluent: 4:1 diisopropyl ether/hexane)
  5. customThe product was obtained in a yield of 145 mg (35%)

Sources & evidence

ORD record
ord-ed9b162d350f47d79ca56e7174287906
Source dataset
uspto-grants-2010_12
Patent number
US07858613B2

Reaction notes

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