Ammonia → 2-Bromo-8alpha-(3,3-diethylureido)-6-methyl-ergoline-13-carbaldehyde

HRID 35851Notes

Reaction equation

HRID 35851 reaction equation
[Br:1][C:2]1[NH:16][C:15]2[C:17]3[C:3]=1[CH2:4][C@@H:5]1[C@@H:10]([C:11]=3[CH:12]=[CH:13][CH:14]=2)[CH2:9][C@H:8]([NH:18][C:19](=[O:25])[N:20]([CH2:23][CH3:24])[CH2:21][CH3:22])[CH2:7][N:6]1[CH3:26].[Cl-].[Al+3].[Cl-].[Cl-].[CH3:31][O:32]C(Cl)Cl.C(O)(=O)C(C(C(O)=O)O)O.N>ClCCl.O>[Br:1][C:2]1[NH:16][C:15]2[C:17]3[C:3]=1[CH2:4][C@@H:5]1[C@@H:10]([C:11]=3[CH:12]=[C:13]([CH:31]=[O:32])[CH:14]=2)[CH2:9][C@H:8]([NH:18][C:19]([N:20]([CH2:23][CH3:24])[CH2:21][CH3:22])=[O:25])[CH2:7][N:6]1[CH3:26]

Participants

8

Reactant 5

HCID 222AmmoniaHCID 8752,3-Dihydroxybutanedioic AcidHCID 21004Methane, dichloromethoxy-HCID 6451240Aluminum(III) ChlorideHCID 130598603-(2-Bromo-6-methyl-8alpha-ergolinyl)-1,1-diethylurea

Product 1

HCID 867486532-Bromo-8alpha-(3,3-diethylureido)-6-methyl-ergoline-13-carbaldehyde

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

838 mg of 3-(2-bromo-6-methyl-8alpha-ergolinyl)-1,1-diethylurea (2 mmol) is dissolved in 100 ml of dichloromethane, 1.2 g of anhydrous aluminum chloride (9 mmol) and 1.8 ml of dichloromethyl methyl ether (20 mmol) are added and stirred for 15 minutes at room temperature. The reaction mixture is mixed with ice and, after 15 minutes, with a solution of 1.5 g of tartaric acid in 50 ml of water and made alkaline with 5 ml of conc. ammonia solution. It is extracted with dichloromethane, the organic phases are dried with sodium sulfate and the solvent is distilled off. The residue is chromatographed on silica gel with dichloromethane/methanol, 406 mg (45% of theory) is isolated.

Workup

  1. extractionIt is extracted with dichloromethane
  2. dry with materialthe organic phases are dried with sodium sulfate
  3. distillationthe solvent is distilled off
  4. customThe residue is chromatographed on silica gel with dichloromethane/methanol
  5. custom406 mg (45% of theory) is isolated

Sources & evidence

ORD record
ord-8ac1f04fc7bf4b3182f969b016355951
Source dataset
uspto-grants-1995_05
Patent number
US05411966

Reaction notes

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