Dimethyl Sulfoxide → HCID 18780220, compound

HRID 1421194Notes

Reaction equation

HRID 1421194 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11]2[C:12](=[O:34])[NH:13][C:14](=[O:33])[C:15]=2[C:16]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[N:18]([CH2:25]CCOS(C)(=O)=O)[CH:17]=2)=[CH:3]1.[S:35]1[CH:39]=[CH:38][CH:37]=[C:36]1CC([O-])=O.[K+].CS(C)=[O:47]>O>[C:36]([S:35][CH2:39][CH2:38][CH2:25][N:18]1[C:19]2[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:16]([C:15]2[C:14](=[O:33])[NH:13][C:12](=[O:34])[C:11]=2[C:4]2[C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[N:2]([CH3:1])[CH:3]=2)=[CH:17]1)(=[O:47])[CH3:37]

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 151630513-(1-methyl-3-indolyl)-4-[1-[3-(methylsulphonyloxy)propyl]-3-indolyl]-1H-pyrrole-2,5-dioneHCID 23696799Potassium 2-thienylacetate

Product 1

HCID 18780220HCID 18780220, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

838 mg of the product of Example 58 in 15 ml of DMSO were treated with 600 mg of potassium thiolacetate. The solution was stirred for 3 hours and then diluted with water. The solution was extracted with ethyl acetate and the ethyl acetate extracts were dried. Concentration and chromatography on silica gel with ethyl acetate gave 723 mg of 3-[1-[3-(acetylthio)propyl]-3-indolyl]-4-(1-methyl-3-indolyl)-1H-pyrrole-2,5-dione, m.p. 210°-213° C.

Workup

  1. extractionThe solution was extracted with ethyl acetate
  2. dry with materialthe ethyl acetate extracts were dried
  3. concentrationConcentration and chromatography on silica gel with ethyl acetate

Sources & evidence

ORD record
ord-7054304260b5487b95e8fe87b0b38346
Source dataset
uspto-grants-2000_06
Patent number
USRE036736

Reaction notes

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