Acetic Anhydride → HCID 18607002, compound

HRID 1906413Notes

Reaction equation

HRID 1906413 reaction equation
Cl.[OH:2][C@@H:3]1[C@H:9]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)[S:8][C:7]2[C:18]3[C:23]([CH:24]=[CH:25][C:6]=2[N:5]([CH2:26][CH2:27][CH2:28][N:29]([CH3:31])[CH3:30])[C:4]1=[O:32])=[CH:22][CH:21]=[CH:20][CH:19]=3.[C:33](OC(=O)C)(=[O:35])[CH3:34]>>[C:33]([O:2][C@@H:3]1[C@H:9]([C:10]2[CH:11]=[CH:12][C:13]([O:16][CH3:17])=[CH:14][CH:15]=2)[S:8][C:7]2[C:18]3[C:23]([CH:24]=[CH:25][C:6]=2[N:5]([CH2:26][CH2:27][CH2:28][N:29]([CH3:30])[CH3:31])[C:4]1=[O:32])=[CH:22][CH:21]=[CH:20][CH:19]=3)(=[O:35])[CH3:34]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 18607007HCID 18607007, compound

Product 1

HCID 18607002HCID 18607002, compoundYield 84%

Procedure

A mixture of 2.6 g of (±)-cis-2,3-dihydro-3-hydroxy-5-[3-(dimethylamino)propyl]-2-(4-methoxyphenyl)naphtho[1,2-b]-1,4-thiazepin-4(5H)-one hydrochloride and 25 mL of acetic anhydride was stirred and heated at 100° for 17 hours. The excess of reagent was removed under reduced pressure and the residue was dissolved in water. The aqueous solution was made basic with concentrated ammonium hydroxide and extracted with ethyl acetate (3×75 mL). The combined ethyl acetate solutions were washed with brine (50 mL) and dried (magnesium sulfate). Removal of the solvent gave 2.2 g (84%) (±)-cis-3-(acetyloxy)-2,3-dihydro-5-[3-(dimethylamino)propyl]-2-(4-methoxyphenyl)naphtho[1,2-b]-1,4-thiazepin-4(5H)-one. A sample of this compound was crystallized from ether, mp 98°-99°.

Workup

  1. temperatureheated at 100° for 17 hours
  2. customThe excess of reagent was removed under reduced pressure
  3. dissolutionthe residue was dissolved in water
  4. extractionextracted with ethyl acetate (3×75 mL)
  5. washThe combined ethyl acetate solutions were washed with brine (50 mL)
  6. dry with materialdried (magnesium sulfate)
  7. customRemoval of the solvent

Sources & evidence

ORD record
ord-913accaef5004886869c337b38413089
Source dataset
uspto-grants-1987_03
Patent number
US04652561

Reaction notes

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