Acetic Acid → HCID 13882044, compound

HRID 231062Notes

Reaction equation

HRID 231062 reaction equation
[Br:1][C:2]1[C:15]2[S:14][C:13]3[C:8](=[CH:9][CH:10]=[C:11]([O:16][CH3:17])[CH:12]=3)[N:7]([C:18]([O:20][CH:21](Cl)[CH3:22])=[O:19])[C:6]=2[CH:5]=[C:4]([O:24][CH3:25])[C:3]=1[OH:26].[C:27]([OH:30])(=[O:29])[CH3:28]>C(OCC)(=O)C>[C:27]([O:30][CH:21]([O:20][C:18]([N:7]1[C:6]2[CH:5]=[C:4]([O:24][CH3:25])[C:3]([OH:26])=[C:2]([Br:1])[C:15]=2[S:14][C:13]2[C:8]1=[CH:9][CH:10]=[C:11]([O:16][CH3:17])[CH:12]=2)=[O:19])[CH3:22])(=[O:29])[CH3:28]

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 14497699HCID 14497699, compound

Product 1

HCID 13882044HCID 13882044, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-bromo-10-(1-chloroethoxycarbonyl)-2,7-dimethoxy-3-hydroxy-10H-phenothiazine (1g) and mercuric acetate (1.46g) in glacial acetic acid (30 ml) was stirred and heated at 85° for 10 minutes. After cooling the mixture was diluted with ethyl acetate, washed with water, aqueous NaHCO3 solution, and brine, dried and evaporated. Flash chromatography on a column of silica gel, eluting with a 1:3 mixture of ethyl acetate and hexane, afforded the pure title product (599 mg) m.p.: 162°-164° C.

Workup

  1. temperatureheated at 85° for 10 minutes
  2. temperatureAfter cooling the mixture
  3. washwashed with water, aqueous NaHCO3 solution, and brine
  4. customdried
  5. customevaporated
  6. washFlash chromatography on a column of silica gel, eluting with a 1:3 mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-2b059a3b2ba74934b4f26b17a056693e
Source dataset
uspto-grants-1989_07
Patent number
US04845083

Reaction notes

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