Ammonia → HCID 67788002, compound

HRID 35855Notes

Reaction equation

HRID 35855 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[C:5](Cl)(=[O:7])[CH3:6].[CH2:9]([N:11]([CH2:33][CH3:34])[C:12]([NH:14][C@H:15]1[CH2:29][C@H:28]2[C@@H:18]([CH2:19][C:20]3[C:30]4[C:23](=[CH:24][CH:25]=[CH:26][C:27]2=4)[NH:22][C:21]=3[CH3:31])[N:17]([CH3:32])[CH2:16]1)=[O:13])[CH3:10].C(O)(=O)C(C(C(O)=O)O)O.N>ClCCl.O>[C:5]([C:25]1[CH:24]=[C:23]2[C:30]3[C:20]([CH2:19][C@@H:18]4[C@@H:28]([C:27]=3[CH:26]=1)[CH2:29][C@H:15]([NH:14][C:12](=[O:13])[N:11]([CH2:33][CH3:34])[CH2:9][CH3:10])[CH2:16][N:17]4[CH3:32])=[C:21]([CH3:31])[NH:22]2)(=[O:7])[CH3:6]

Participants

8

Reactant 5

HCID 222AmmoniaHCID 8752,3-Dihydroxybutanedioic AcidHCID 6367Acetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 140110111,1-Diethyl-3-(2,6-dimethyl-8alpha-ergolinyl)urea

Product 1

HCID 67788002HCID 67788002, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

2.4 g of anhydrous aluminum chloride and 1.3 ml of acetyl chloride are dissolved in 70 ml of dichloromethane and stirred for 15 minutes at room temperature. 708 mg of 1,1-diethyl-3-(2,6-dimethyl-8alpha-ergolinyl)-urea (2 mmol) dissolved in 30 ml of dichloromethane is added to it, and stirred for 30 minutes at room temperature. Ice is added and after 15 minutes of stirring, a solution of 2.8 g of tartaric acid in 80 ml of water is added. After another 15 minutes, it is made alkaline with conc. ammonia, the organic phase is separated and the water phase is extracted. All organic phases are dried with sodium sulfate and concentrated by evaporation, the residue is chromatographed on silica gel with dichloromethane/methanol, yield 454 mg.

Workup

  1. additionis added to it
  2. stirringstirred for 30 minutes at room temperature
  3. additionIce is added and after 15 minutes
  4. stirringof stirring
  5. waitAfter another 15 minutes
  6. customthe organic phase is separated
  7. extractionthe water phase is extracted
  8. dry with materialAll organic phases are dried with sodium sulfate
  9. concentrationconcentrated by evaporation
  10. customthe residue is chromatographed on silica gel with dichloromethane/methanol, yield 454 mg

Sources & evidence

ORD record
ord-2cfae1d54abc402598870d7d241f230e
Source dataset
uspto-grants-1995_05
Patent number
US05411966

Reaction notes

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