Hydrogen Bromide → HCID 13823186, compound

HRID 649507Notes

Reaction equation

HRID 649507 reaction equation
[CH2:1]([N:3]([CH2:24][CH3:25])[C:4]([NH:6][C@H:7]1[CH2:21][C@H:20]2[C@@H:10]([CH2:11][C:12]3[C:22]4[C:15](=[CH:16][CH:17]=[CH:18][C:19]2=4)[NH:14][CH:13]=3)[N:9]([CH3:23])[CH2:8]1)=[O:5])[CH3:2].[BrH:26].[Br:27]Br.C(OC(C)C)(C)C>C(Cl)Cl.C(O)(=O)C>[Br:26][C:13]1[NH:14][C:15]2[C:22]3[C:12]=1[CH2:11][C@@H:10]1[C@@H:20]([C:19]=3[CH:18]=[C:17]([Br:27])[CH:16]=2)[CH2:21][C@H:7]([NH:6][C:4](=[O:5])[N:3]([CH2:1][CH3:2])[CH2:24][CH3:25])[CH2:8][N:9]1[CH3:23]

Participants

7

Reactant 4

HCID 260Hydrogen BromideHCID 7914Diisopropyl EtherHCID 24408BromineHCID 443951Terguride

Product 1

HCID 13823186HCID 13823186, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent2×

Procedure

10 g of 1,1-diethyl-3-(6-methyl-8α-ergolinyl)urea (terguride) (30 mmol) is dissolved in 550 ml of methylene chloride and, under ice cooling, 8.8 ml of 33% strength solution of hydrogen bromide in glacial acetic acid is added thereto. With continued cooling, a solution of 3.1 ml of bromine (60 mmol) in 400 ml of methylene chloride is added dropwise thereto within 30 minutes. The crystalline slurry is combined with 200 ml of diisopropyl ether, and the crystals are filtered off after stirring for 20 minutes. Recrystallization from methylene chloride, methanol and diisopropyl ether yields 10.5 g of 3-(2,13-dibromo-6-methyl-8α-ergolinyl)-1,1-diethylurea (71% of theory).

Workup

  1. temperatureWith continued cooling
  2. filtrationthe crystals are filtered off
  3. customRecrystallization from methylene chloride, methanol and diisopropyl ether

Sources & evidence

ORD record
ord-e903cd6b0eaf4b1a94aff50a54a1f803
Source dataset
uspto-grants-1988_04
Patent number
US04740509

Reaction notes

Loading…