Phenyl Isothiocyanate → Phenylthiocarbamic acid O-(4-hydroxymethyl-5-oxo-2,3,4,5-tetrahydro-benzo[b]thiepin-4-ylmethyl)ester

HRID 2265820Notes

Reaction equation

[OH:1][CH2:2][C:3]1([CH2:15][OH:16])[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:24]1([N:30]=[C:31]=[S:32])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>O1CCCC1>[OH:16][CH2:15][C:3]1([CH2:2][O:1][C:31](=[S:32])[NH:30][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[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]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 4,4-bis(hydroxymethyl)-3,4-dihydro-2H-benzo[b]thiepin-5-one (252 mg, 1.06 mmol) in 13 ml of tetrahydrofuran were added, at room temperature, triethylamine (0.16 ml, 1.16 mmol) and phenyl isothiocyanate (277 μl, 2.3 mmol). The mixture was stirred at 80° C. for 36 hours, concentrated and purified by column chromatography on silica gel (eluent: 4:1 diisopropyl ether/hexane). The product was obtained in a yield of 48 mg (12%).

Workup

concentrationconcentrated
custompurified by column chromatography on silica gel (eluent: 4:1 diisopropyl ether/hexane)
customThe product was obtained in a yield of 48 mg (12%)

Sources & evidence

ORD record: ord-0ecd9457c7824063995ed95db7cc9e52
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07858613B2

Reaction notes

Loading…