Acetic Anhydride → HCID 18607010, compound

HRID 1906410Notes

Reaction equation

HRID 1906410 reaction equation
[ClH:1].[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][N:28]([CH2:31][CH3:32])[CH2:29][CH3:30])[C:4]1=[O:33])=[CH:22][CH:21]=[CH:20][CH:19]=3.[C:34](OC(=O)C)(=[O:36])[CH3:35]>>[ClH:1].[C:34]([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][N:28]([CH2:31][CH3:32])[CH2:29][CH3:30])[C:4]1=[O:33])=[CH:22][CH:21]=[CH:20][CH:19]=3)(=[O:36])[CH3:35]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 18607006HCID 18607006, compound

Product 1

HCID 18607010HCID 18607010, compoundYield 93%

Procedure

A mixture of 2.5 g of (±)-cis-2,3-dihydro-3-hydroxy-2-(4-methoxyphenyl)-5-[2-(diethylamino)ethyl]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 crystallized from ethyl acetate to give 2.5 g (93%) of (±)-cis-3-(acetyloxy)-5-[2-(diethylamino)ethyl]-2,3-dihydro-2-(4-methoxyphenyl)naphtho[1,2-b]-1,4-thiazepin-4(5H)-one hydrochloride, mp 211°-212°.

Workup

  1. temperatureheated at 100° for 17 hours
  2. customThe excess of reagent was removed under reduced pressure
  3. customthe residue was crystallized from ethyl acetate

Sources & evidence

ORD record
ord-e95905eba6fc45c2b21b16dc84eb4e57
Source dataset
uspto-grants-1987_03
Patent number
US04652561

Reaction notes

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