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Cornforth reagent → 3-(9,10-Didehydro-6-methyl-14-nitro-8alpha-ergolinyl)-1,1-diethylurea

HRID 35214
Notes
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Reaction equation

HRID 35214 reaction equation
[CH3:1][N:2]1[C@H:16]2[C:6]([C:7]3[CH:8]=[CH:9][C:10]([N+:18]([O-:20])=[O:19])=[C:11]4[C:17]=3[CH:14]([CH2:15]2)[CH2:13][NH:12]4)=[CH:5][C@H:4]([NH:21][C:22](=[O:28])[N:23]([CH2:26][CH3:27])[CH2:24][CH3:25])[CH2:3]1.[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1>C(Cl)Cl.O>[CH3:1][N:2]1[C@H:16]2[C:6]([C:7]3[CH:8]=[CH:9][C:10]([N+:18]([O-:20])=[O:19])=[C:11]4[C:17]=3[C:14]([CH2:15]2)=[CH:13][NH:12]4)=[CH:5][C@H:4]([NH:21][C:22](=[O:28])[N:23]([CH2:26][CH3:27])[CH2:24][CH3:25])[CH2:3]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 2724130Cornforth reagentHCID 867423503-(9,10-Didehydro-2,3-dihydro-6-methyl-14-nitro-8alpha-ergolinyl)-1,1-diethylurea

Product 1

HCID 133749593-(9,10-Didehydro-6-methyl-14-nitro-8alpha-ergolinyl)-1,1-diethylureaYield 46.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent
HCID 6344
Dichloromethane
Solvent
2×

Procedure

A solution is prepared from 150 mg of 3-(9,10-didehydro-2,3-dihydro-6-methyl-14-nitro-8α-ergolinyl)-1,1-diethylurea in 5 ml of methylene chloride; 250 mg of pyridinium dichromate, dissolved in 2 ml of methylene chloride, is added to the reaction mixture and the latter is agitated for one hour at room temperature. Then the mixture is diluted with water, extracted by shaking with methylene chloride, the organic phase is dried and evaporated. The residue is chromatographed on silica gel with methylene chloride/methanol (5%), thus obtaining 70 mg of 3-(9,10-didehydro-6-methyl-14-nitro-8α-ergolinyl)-1,1-diethylurea.

Workup

  1. additionis added to the reaction mixture
  2. extractionextracted
  3. stirringby shaking with methylene chloride
  4. customthe organic phase is dried
  5. customevaporated
  6. customThe residue is chromatographed on silica gel with methylene chloride/methanol (5%)

Sources & evidence

ORD record
ord-ccae881c61ab40a7ad74fdb1aa4f7210
Source dataset
uspto-grants-1988_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04766128

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes