Acetic Acid → HCID 20286674, compound

HRID 127300Notes

Reaction equation

HRID 127300 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:12]=[C:11]2[C:7]([C:8]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[C:9]([C:13](OCC)=[O:14])[NH:10]2)=[CH:6][C:5]=1[Cl:24].O.C(O)(=O)C.[CH3:30][S:31]([CH3:33])=[O:32]>C1C=CC=CC=1>[Br:3][C:4]1[CH:12]=[C:11]2[C:7]([C:8]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[C:9]([C:13](=[O:14])[CH2:30][S:31]([CH3:33])=[O:32])[NH:10]2)=[CH:6][C:5]=1[Cl:24]

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 679Dimethyl Sulfoxide2×HCID 962Water2×HCID 24758Sodium hydrideHCID 20286704HCID 20286704, compound

Product 1

HCID 20286674HCID 20286674, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

Stir sodium hydride (13 g) in a mixture of dimethylsulfoxide (100 ml) and benzene (100 ml), and heat at 65°-75° for 2 hours under nitrogen. To this mixture add ethyl 6-bromo-5-chloro-3-phenylindole-2-carboxylate in dimethylsulfoxide (50 ml) and benzene (30 ml) at 15°-20° and stir the mixture at room temperature for one hour. Cool the resulting mixture to 15° C. add 50 ml of water (very slowly) and then add an additional 550 ml of water. Add 25 ml of acetic acid, stir and then filter. Wash the resulting solid with water and then hexane. Crystallize the desired product from methanol-methylene chloride to obtain 6-bromo-5-chloro-2[(methylsulfinyl)acetyl]-3-phenylindole, m.p. 169°-170°.

Workup

  1. temperatureheat at 65°-75° for 2 hours under nitrogen
  2. temperatureCool the resulting mixture to 15° C.
  3. stirringstir
  4. filtrationfilter
  5. washWash the resulting solid with water
  6. customCrystallize the desired product from methanol-methylene chloride

Sources & evidence

ORD record
ord-f6c0c7f532b44fdab4bb7279ed3749ab
Source dataset
uspto-grants-1981_03
Patent number
US04255442

Reaction notes

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