Acetic Anhydride → 5-[2-(Dimethylamino)ethyl]-2-(4-methoxyphenyl)-4-oxo-2,3,4,5-tetrahydronaphtho[1,2-b][1,4]thiazepin-3-yl acetate
Reaction equation
Cl.[CH3:2][N:3]([CH3:31])[CH2:4][CH2:5][N:6]1[C:12](=[O:13])[C@H:11]([OH:14])[C@H:10]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)[S:9][C:8]2[C:23]3[C:28]([CH:29]=[CH:30][C:7]1=2)=[CH:27][CH:26]=[CH:25][CH:24]=3.[C:32](OC(=O)C)(=[O:34])[CH3:33]>>[C:32]([O:14][C@@H:11]1[C@H:10]([C:15]2[CH:16]=[CH:17][C:18]([O:21][CH3:22])=[CH:19][CH:20]=2)[S:9][C:8]2[C:23]3[C:28]([CH:29]=[CH:30][C:7]=2[N:6]([CH2:5][CH2:4][N:3]([CH3:2])[CH3:31])[C:12]1=[O:13])=[CH:27][CH:26]=[CH:25][CH:24]=3)(=[O:34])[CH3:33]Participants
3
Procedure
A mixture of 1.1 g of (±)-cis-5-[2-(dimethylamino)ethyl]-2,3-dihydro-3-hydroxy-2-(4-methoxyphenyl)naphtho[1,2-b]-1,4-thiazepin-4(5H)-one hydrochloride and 20 mL of acetic anhydride was heated at 100° for 17 hours. The excess reagent was removed under reduced pressure and the residue was partitioned between dilute sodium hydroxide and ethyl acetate. The ethyl acetate solution was washed with brine, then dried (magnesium sulfate) and removal of the solvent gave 1.1 g (99%) of (±)-cis-3-(acetyloxy)-2,3-dihydro-2-(4-methoxyphenyl)-5-[2-(dimethylamino)ethyl]-naphtho[1,2-b]-1,4-thiazepin-4(5H)-one. A sample was crystallized from ether, mp 122°-124°.
Workup
- temperaturewas heated at 100° for 17 hours
- customThe excess reagent was removed under reduced pressure
- customthe residue was partitioned between dilute sodium hydroxide and ethyl acetate
- washThe ethyl acetate solution was washed with brine
- customdried
- custom(magnesium sulfate) and removal of the solvent
Sources & evidence
- ORD record
- ord-851fe36a337c4d06ad44d5da4077e316
- Source dataset
- uspto-grants-1987_03
- Patent number
- US04652561
Reaction notes
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