Water → HCID 53909432, compound

HRID 247012Notes

Reaction equation

HRID 247012 reaction equation
O.S([O-])([O-])=O.[Na+].[Na+].[Br:8][C:9]1[CH:14]=[CH:13][C:12]([S:15]([C:18]2[CH:19]=[C:20]([S:24](Cl)(=[O:26])=[O:25])[CH:21]=[CH:22][CH:23]=2)(=[O:17])=[O:16])=[CH:11][CH:10]=1.Cl[CH2:29][C:30]([O:32][CH3:33])=[O:31]>C(#N)C>[CH3:33][O:32][C:30](=[O:31])[CH2:29][S:24]([C:20]1[CH:21]=[CH:22][CH:23]=[C:18]([S:15]([C:12]2[CH:13]=[CH:14][C:9]([Br:8])=[CH:10][CH:11]=2)(=[O:17])=[O:16])[CH:19]=1)(=[O:26])=[O:25]

Participants

6

Reactant 4

HCID 962Water2×HCID 7295Methyl chloroacetateHCID 24437Sodium SulfiteHCID 15527423HCID 15527423, compound

Product 1

HCID 53909432HCID 53909432, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

To 150 ml of water was added 85 g of sodium sulfite and then 54 g of 3-(4-bromophenylsulfonyl)benzenesulfonyl chloride was added thereto. After stirring the mixture for 2 hours at 50° C., the reaction mixture thus obtained was ice-cooled and crystals thus formed were collected by filtration. To the crystals thus obtained were added 40 ml of water, 40 ml of acetonitrile and 15 ml of methyl chloroacetate followed by refluxing for 2 hours. The reaction mixture thus formed was extracted with chloroform and then chloroform was distilled off from the extract to provide 32.7 g of oily 3-(4-bromophenylsulfonyl)phenylsulfonylacetic acid methyl ester. Then, the oily product thus obtained was added to a mixture of 60 ml of water, 60 ml of methanol, and 8.1 g of potassium hydroxide and the resultant mixture was stirred for one hour at room temperature. After adding 20 ml of 35% hydrochloric acid to the reaction mixture, the mixture was ice-cooled and crystals thus deposited were collected by filtration to provide 25.4 g of 3-(4-bromophenylsulfonyl)phenylsulfonylacetic acid. By neutralizing 21 g of the crystals thus obtained with 4.5 g of guanidine carbonate as in Synthesis Example 3 22.3 g of Base Precursor (123) was obtained. The melting point was 85° C. and the decomposition point was 95° C.

Workup

  1. customthe reaction mixture thus obtained
  2. temperaturecooled
  3. customcrystals thus formed
  4. filtrationwere collected by filtration
  5. customTo the crystals thus obtained
  6. temperatureby refluxing for 2 hours
  7. customThe reaction mixture thus formed
  8. extractionwas extracted with chloroform
  9. distillationchloroform was distilled off from the
  10. extractionextract

Sources & evidence

ORD record
ord-b00a4205739248ae82e9ff7e65a3edfa
Source dataset
uspto-grants-1987_11
Patent number
US04705737

Reaction notes

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