Acetic Anhydride → HCID 86741355, compound

HRID 1906404Notes

Reaction equation

HRID 1906404 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

Reactant 2

HCID 7918Acetic AnhydrideHCID 86741356HCID 86741356, compound

Product 1

HCID 86741355HCID 86741355, compoundYield 91%

Procedure

A mixture of 1.1 g of (±)-trans-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 acetic anhydride was heated at 100° for 17 hours. The excess reagent was removed under reduced pressure and the residue was partitioned between ethyl acetate and dilute sodium hydroxide. The ethyl acetate solution was washed with brine and dried (magnesium sulfate). Removal of the solvent gave 1.0 g (91%) of (±)-trans-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--pet. ether, mp 122°-123°.

Workup

  1. temperaturewas heated at 100° for 17 hours
  2. customThe excess reagent was removed under reduced pressure
  3. customthe residue was partitioned between ethyl acetate and dilute sodium hydroxide
  4. washThe ethyl acetate solution was washed with brine
  5. dry with materialdried (magnesium sulfate)
  6. customRemoval of the solvent

Sources & evidence

ORD record
ord-41a7fc3e7c3749ecbd026c4de1de9db9
Source dataset
uspto-grants-1987_03
Patent number
US04652561

Reaction notes

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