Carbonyl bromide → HCID 22254060, compound

HRID 457682

Reaction equation

HRID 457682 reaction equation
[NH2:1][C:2]([NH2:4])=[S:3].[CH:5]([C:8]([NH:10][CH:11]1[CH2:16][CH2:15][CH:14](N(C)C(N)=S)[CH2:13][CH2:12]1)=[O:9])([CH3:7])[CH3:6].Br[C:23](Br)=O.C(N(C(C)C)CC)(C)C>CCO>[CH:5]([C:8]([NH:10][CH:11]1[CH2:16][CH2:15][CH:14]([CH2:23][NH:1][C:2]([NH2:4])=[S:3])[CH2:13][CH2:12]1)=[O:9])([CH3:7])[CH3:6]

Participants

6

Reactant 4

HCID 79057Carbonyl bromideHCID 81531DiisopropylethylamineHCID 2723790ThioureaHCID 17946834HCID 17946834, compound

Product 1

HCID 22254060HCID 22254060, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A thiourea such as N-[4-(isopropylformylamino)cyclohexyl]-methylthiourea (0.029 mmol, 1 equivalent), a bromoketone (0.044 mmol, 1.5 equivalent) and 2 equivalents of diisopropylethyl amine in 10 ml of EtOH were heated at reflux temperature for 2 days. The reaction mixture was concentrated in vacuo and the crude product chromatographed (silica) to obtain the desired product. This procedure was used to prepare examples 101–102.

Workup

  1. temperatureat reflux temperature for 2 days
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customthe crude product chromatographed (silica)

Sources & evidence

ORD record
ord-ee9773061a0943b58a1861525ed730a9
Source dataset
uspto-grants-2007_03
Patent number
US07189720B2

Linked notes

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