Bromine → HCID 13823184, compound

HRID 649505Notes

Reaction equation

HRID 649505 reaction equation
[CH3:1][N:2]1[C@H:16]2[C@@H:6]([C:7]3[CH:8]=[CH:9][CH:10]=[C:11]4[C:17]=3[C:14]([CH2:15]2)=[C:13]([S:18][CH3:19])[NH:12]4)[CH2:5][C@H:4]([NH:20][C:21](=[O:27])[N:22]([CH2:25][CH3:26])[CH2:23][CH3:24])[CH2:3]1.[Br:28]Br>C(Cl)Cl>[Br:28][C:9]1[CH:10]=[C:11]2[C:17]3[C:14]([CH2:15][C@@H:16]4[C@@H:6]([C:7]=3[CH:8]=1)[CH2:5][C@H:4]([NH:20][C:21](=[O:27])[N:22]([CH2:23][CH3:24])[CH2:25][CH3:26])[CH2:3][N:2]4[CH3:1])=[C:13]([S:18][CH3:19])[NH:12]2

Participants

4

Reactant 2

HCID 24408BromineHCID 13559018HCID 13559018, compound

Product 1

HCID 13823184HCID 13823184, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution is prepared from 11.2 g of 3-(6-methyl-2-methylthio-8α-ergolinyl)-1,1-diethylurea (29 mmol) in 400 ml of methylene chloride p.a. and, at room temperature, 1.45 ml of bromine (26 mmol) dissolved in 100 ml of methylene chloride p.a. is added dropwise thereto within 20 minutes. After 15 minutes of agitation, the solvent is distilled off under vacuum, the residue is taken up in methylene chloride and methanol, and crystallized by adding ethyl acetate with a small amount of diisopropyl ether and by removing the readily volatile solvents by distillation.

Workup

  1. additionis added dropwise
  2. waitAfter 15 minutes of agitation
  3. distillationthe solvent is distilled off under vacuum
  4. custommethanol, and crystallized
  5. additionby adding ethyl acetate with a small amount of diisopropyl ether
  6. customby removing the readily volatile solvents
  7. distillationby distillation

Sources & evidence

ORD record
ord-3e47d1947ce6412bbd5e3a90b803f94a
Source dataset
uspto-grants-1988_04
Patent number
US04740509

Reaction notes

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