Thiourea → HCID 86745174, compound

HRID 1421173Notes

Reaction equation

HRID 1421173 reaction equation
[NH2:1][C:2]([NH2:4])=[S:3].[CH3:5][S:6]([O:9][CH2:10][CH2:11][CH2:12][N:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]([C:22]2[C:23](=[O:37])[NH:24][C:25](=[O:36])[C:26]=2[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[N+:33]([O-:35])=[O:34])=[CH:14]1)(=[O:8])=[O:7]>C(O)C>[CH3:5][S:6]([OH:9])(=[O:8])=[O:7].[C:2]([S:3][CH2:10][CH2:11][CH2:12][N:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]([C:22]2[C:23](=[O:37])[NH:24][C:25](=[O:36])[C:26]=2[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[N+:33]([O-:35])=[O:34])=[CH:14]1)(=[NH:4])[NH2:1]

Participants

4

Reactant 2

HCID 2723790ThioureaHCID 18780248HCID 18780248, compound

Product 1

HCID 86745174HCID 86745174, compoundYield 5.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

50 mg of thiourea were added to a solution, heated at reflux, of 150 mg of the product of Example 68 in 15 ml of ethanol. The mixture was heated for 1 hour and the solvent was then evaporated. The residue was chromatographed on silica gel with 20% methanol in dichloromethane to give 10 mg of 3-[1-[3-(amidinothio)propyl]-3-indolyl]-4-(2-nitrophenyl)-1H-pyrrole-2,5-dione methanesulphonate, m.p. 164°-165° C.

Workup

  1. temperatureheated
  2. temperatureThe mixture was heated for 1 hour
  3. customthe solvent was then evaporated
  4. customThe residue was chromatographed on silica gel with 20% methanol in dichloromethane

Sources & evidence

ORD record
ord-f0bc4a4b3a514d0c83c27fad8ba92589
Source dataset
uspto-grants-2000_06
Patent number
USRE036736

Reaction notes

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