Sodium Acetate → HCID 13712495, compound

HRID 64972Notes

Reaction equation

HRID 64972 reaction equation
[OH:1][C:2]1[CH:15]=[C:14]2[C:5]([N:6]([C:16]([O:18][CH:19](Cl)[CH3:20])=[O:17])[C:7]3[C:12]([S:13]2)=[CH:11][CH:10]=[CH:9][CH:8]=3)=[C:4]2[CH:22]=[CH:23][CH:24]=[CH:25][C:3]=12.[C:26]([O-:29])(=[O:28])[CH3:27].[Na+]>C(O)(=O)C.C(OCC)(=O)C>[OH:1][C:2]1[CH:15]=[C:14]2[C:5]([N:6]([C:16]([O:18][CH:19]([O:29][C:26](=[O:28])[CH3:27])[CH3:20])=[O:17])[C:7]3[C:12]([S:13]2)=[CH:11][CH:10]=[CH:9][CH:8]=3)=[C:4]2[CH:22]=[CH:23][CH:24]=[CH:25][C:3]=12

Participants

5

Reactant 2

HCID 517045Sodium AcetateHCID 146014145-hydroxy-12-(alpha-chloroethoxycarbonyl)-12H-benzo[a]phenothiazine

Product 1

HCID 13712495HCID 13712495, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

The product from Step 2 (4 g) and sodium acetate (6 g) were refluxed together in glacial acetic acid (60 ml) for 1 hour. The mixture was cooled, diluted with ethyl acetate (300 ml) and washed with water (3×100 ml), then with aqueous sodium bicarbonate and again with water, dried and evaporated down. The residue was chromatographed on a column of silica gel eluting with a 1:9 mixture of ethyl acetate-hexane to afford, after trituration in ether and filtration, the pure title compound (1.2 g), m.p. 195°-196° C.

Workup

  1. temperatureThe mixture was cooled
  2. washwashed with water (3×100 ml)
  3. dry with materialwith aqueous sodium bicarbonate and again with water, dried
  4. customevaporated down
  5. customThe residue was chromatographed on a column of silica gel eluting with a 1:9 mixture of ethyl acetate-hexane
  6. customto afford
  7. filtrationafter trituration in ether and filtration

Sources & evidence

ORD record
ord-4e80cd9b99b141a39967b004768d25dd
Source dataset
uspto-grants-1986_09
Patent number
US04611056

Reaction notes

Loading…