1-Bromopropane → 10-Propyl-dibenz(b,f)(1,4)thiazepin-11-(10H)-one

HRID 1898864Notes

Reaction equation

[H-].[Na+].[CH:3]1[C:8]2[C:9](=[O:18])[NH:10][C:11]3[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=3[S:13][C:7]=2[CH:6]=[CH:5][CH:4]=1.Br[CH2:20][CH2:21][CH3:22]>CN(C)C=O>[CH2:20]([N:10]1[C:9](=[O:18])[C:8]2[CH:3]=[CH:4][CH:5]=[CH:6][C:7]=2[S:13][C:12]2[CH:14]=[CH:15][CH:16]=[CH:17][C:11]1=2)[CH2:21][CH3:22]

Participants

Conditions

Temperature: 50 °C

Procedure

0.14 grams of a 50% dispersion of sodium hydride in mineral oil was added to a solution of dibenz[b,f][1,4]thiazepin-11(10H)-one in 10 ml of dimethylformamide. After 15 minutes the mixture was warmed to 50° C. and stirred under argon for one hour. After allowing the mixture to cool to room temperature, 0.34 grams of 1-bromopropane was added slowly. The reaction mixture was stirred for 5 hours, after which time it was quenched with water and the product extracted with diethyl ether. The extracts were washed with a saline solution, dried (anhydrous magnesium sulfate) and concentrated to give a colorless oil which was purified by column chromatography (ethyl acetate/hexane, 5%, 10%, 20%) to provide 0.37 grams (91% of theory) of 10-n-propyl-dibenz[b,f][1,4]thiazepin-11(10H)-one as a white crystalline solid, m.p. 103°-104.5° C.

Workup

temperatureto cool to room temperature
stirringThe reaction mixture was stirred for 5 hours
customafter which time it was quenched with water
extractionthe product extracted with diethyl ether
washThe extracts were washed with a saline solution
dry with materialdried (anhydrous magnesium sulfate)
concentrationconcentrated
customto give a colorless oil which
customwas purified by column chromatography (ethyl acetate/hexane, 5%, 10%, 20%)

Sources & evidence

ORD record: ord-6db6e83d82ec49f3b729789578549e3e
Source dataset: uspto-grants-1996_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05571806

Reaction notes

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