Ammonia → HCID 13823196, compound

HRID 649508Notes

Reaction equation

HRID 649508 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]([Br:20])=[CH:16][CH:17]=2)[CH2:12][C@H:11]([NH:21][C:22](=[O:28])[N:23]([CH2:26][CH3:27])[CH2:24][CH3:25])[CH2:10][N:9]4[CH3:29])[CH2:5]1)(=O)C.N>Cl>[Br:20][C:15]1[C:14]2=[C:19]3[C:18]([NH:4][CH2:5][C@@H:6]3[CH2:7][C@@H:8]3[C@@H:13]2[CH2:12][C@H:11]([NH:21][C:22](=[O:28])[N:23]([CH2:26][CH3:27])[CH2:24][CH3:25])[CH2:10][N:9]3[CH3:29])=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 13823193HCID 13823193, compound

Product 1

HCID 13823196HCID 13823196, compoundYield 18.3%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of 1.8 g of 3-(1-acetyl-12-bromo-2,3α-dihydro-6-methyl-8α-ergolinyl)-1,1-diethylurea in 50 ml of 1N hydrochloric acid is stirred for 4 hours at 70°-80° C. The reaction mixture is poured on 100 ml of ice, combined with 25% strength ammonia solution until the reaction is alkaline, and extracted with dichloromethane. The combined organic phases are dried over magnesium sulfate, concentrated, and the residue chromatographed on silica gel with dichloromethane/methanol in a ratio of 97:3, thus isolating 300 mg of an oily product which, for complete purification, is crystallized from ethyl acetate/diisopropyl ether. Yield: 200 mg of 3-(12-bromo-2,3α-dihydro-6-methyl-8α-ergolinyl)-1,1-diethylurea.

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialThe combined organic phases are dried over magnesium sulfate
  3. concentrationconcentrated
  4. customthe residue chromatographed on silica gel with dichloromethane/methanol in a ratio of 97:3

Sources & evidence

ORD record
ord-cbf543a6795046b1a1c51a8120f779fc
Source dataset
uspto-grants-1988_04
Patent number
US04740509

Reaction notes

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