Water → 3-(2,3-Dihydro-6-methyl-12-nitro-8alpha-ergolinyl)-1,1-diethylurea

HRID 35211Notes

Reaction equation

HRID 35211 reaction equation
C([N:4]1[C:18]2[C:19]3[C@H:6]([CH2:7][C@@H:8]4[C@@H:13]([C:14]=3[C:15]([N+:20]([O-:22])=[O:21])=[CH:16][CH:17]=2)[CH2:12][C@H:11]([NH:23][C:24](=[O:30])[N:25]([CH2:28][CH3:29])[CH2:26][CH3:27])[CH2:10][N:9]4[CH3:31])[CH2:5]1)(=O)C.O>NN.C(Cl)(Cl)Cl>[CH3:31][N:9]1[C@H:8]2[C@@H:13]([C:14]3[C:15]([N+:20]([O-:22])=[O:21])=[CH:16][CH:17]=[C:18]4[C:19]=3[CH:6]([CH2:7]2)[CH2:5][NH:4]4)[CH2:12][C@H:11]([NH:23][C:24](=[O:30])[N:25]([CH2:28][CH3:29])[CH2:26][CH3:27])[CH2:10]1

Participants

5

Reactant 2

HCID 962WaterHCID 867423483-(1-Acetyl-2,3beta-dihydro-6-methyl-12-nitro-8alpha-ergolinyl)-1,1-diethylurea

Product 1

HCID 867423473-(2,3-Dihydro-6-methyl-12-nitro-8alpha-ergolinyl)-1,1-diethylureaYield 59.4%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 9321HydrazineSolvent

Procedure

One millimole of 3-(1-acetyl-2,3β-dihydro-6-methyl-12-nitro-8α-ergolinyl)-1,1-diethylurea is heated in a mixture of 2 ml of anhydrous hydrazine and 2 ml of chloroform for 3 hours to 50° C., poured into water, extracted with methylene chloride, the organic phase is dried, and evaporated under vacuum, yielding 230 mg of 3-(2,3-dihydro-6-methyl-12-nitro-8α-ergolinyl)-1,1-diethylurea. Yield: 25%. [α]D =+538° (0.5% in methanol) as the tartaric acid salt.

Workup

  1. extractionextracted with methylene chloride
  2. customthe organic phase is dried
  3. customevaporated under vacuum

Sources & evidence

ORD record
ord-aa4f510690ae470597a3bd9ef67cf53f
Source dataset
uspto-grants-1988_08
Patent number
US04766128

Reaction notes

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