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

HRID 35212Notes

Reaction equation

HRID 35212 reaction equation
C([N:4]1[C:18]2[C:19]3[CH: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.N.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 3

HCID 222AmmoniaHCID 6344DichloromethaneHCID 867423493-(1-Acetyl-2,3-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 56.8%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

One millimole of 3-(1-acetyl-2,3-dihydro-6-methyl-12-nitro-8α-ergolinyl)-1,1-diethylurea, dissolved in 5 ml of 1N hydrochloric acid, is heated for one hour to 95° C. After cooling, the mixture is made alkaline with dilute ammonia solution, combined with methylene chloride, and extracted. After drying the organic phase, the latter is evaporated, thus obtaining 220 mg of 3-(2,3-dihydro-6-methyl-12-nitro-8α-ergolinyl)-1,1-diethylurea.

Workup

  1. temperatureis heated for one hour to 95° C
  2. temperatureAfter cooling
  3. extractionextracted
  4. customAfter drying the organic phase
  5. customthe latter is evaporated

Sources & evidence

ORD record
ord-50430ceabdde4460a706143f93abddfa
Source dataset
uspto-grants-1988_08
Patent number
US04766128

Reaction notes

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