Dimethyl Sulfoxide → HCID 18780220, compound

HRID 345707Notes

Reaction equation

HRID 345707 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-6c421a4e2149406ebcb5b165958dda3b
Source dataset
uspto-grants-1991_10
Patent number
US05057614

Reaction notes

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