Ammonia → 3-(2-Bromo-13-chloro-6-methyl-8alpha-ergolinyl)-1,1-diethylurea

HRID 35858

Reaction equation

HRID 35858 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:27]N1C(=O)N(Cl)C(=O)N(Cl)C1=O.N.ClCCl>FC(F)(F)C(O)=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]([Cl:27])[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]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 6344DichloromethaneHCID 6909Trichloroisocyanuric AcidHCID 130598603-(2-Bromo-6-methyl-8alpha-ergolinyl)-1,1-diethylurea

Product 1

HCID 677885733-(2-Bromo-13-chloro-6-methyl-8alpha-ergolinyl)-1,1-diethylurea

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

2.1 g of 3-(2-bromo-6-methyl-8alpha-ergolinyl)-1,1-diethylurea (5 mmol) and 388 mg of trichloroisocyanuric acid (1.67 mmol) are dissolved in 100 ml of trifluoroacetic acid at room temperature. After 15 minutes, ice is added, it is made alkaline with conc. ammonia and shaken out with dichloromethane. The organic phases are dried and concentrated by evaporation, the residue is chromatographed and the product crystallizes from ethyl acetate/ether, yield 480 mg (21% of theory).

Workup

  1. additionice is added
  2. customThe organic phases are dried
  3. concentrationconcentrated by evaporation
  4. customthe residue is chromatographed
  5. customthe product crystallizes from ethyl acetate/ether, yield 480 mg (21% of theory)

Sources & evidence

ORD record
ord-e4f87c257b9c434bb882cda9bcf99f6e
Source dataset
uspto-grants-1995_05
Patent number
US05411966

Linked notes

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