Ethanol → HCID 10159221, compound

HRID 2183659Notes

Reaction equation

HRID 2183659 reaction equation
[Br:1][CH:2]([CH3:16])[C:3]([C:5]1[S:9][C:8]2[CH:10]=[CH:11][C:12]([Cl:15])=[C:13]([Cl:14])[C:7]=2[CH:6]=1)=O.[NH:17]1[CH2:21][CH2:20][NH:19][C:18]1=[S:22].C(O)C>C(O)(=O)C>[BrH:1].[Cl:14][C:13]1[C:7]2[CH:6]=[C:5]([C:3]3[N:19]4[CH2:20][CH2:21][N:17]=[C:18]4[S:22][C:2]=3[CH3:16])[S:9][C:8]=2[CH:10]=[CH:11][C:12]=1[Cl:15]

Participants

5

Reactant 3

HCID 702EthanolHCID 2723650EthylenethioureaHCID 22473920HCID 22473920, compound

Product 1

HCID 10159221HCID 10159221, compoundYield 101.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 2-bromo-1-(4,5-dichlorobenzo[b]thiophen-2-yl)propan-1-one (1.59 g), 2-imidazolidinethione (0.43 g), ethanol (25 ml) and acetic acid (12.5 ml) was heated under reflux for 4 hours and allowed to cool to ambient temperature. The solvent was removed in vacuo to give a yellow solid which was triturated with ether (3×10 ml). The resulting solid was collected by filtration and dried in vacuo at 60° C. to give 3-(4,5-dichlorobenzo[b]thiophen-2-yl)-2-methyl-5,6-dihydroimidazo[2,1-b]-thiazole hydrobromide (1.8 g) as a yellow solid, m.p. 244-246° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 4 hours
  3. customThe solvent was removed in vacuo
  4. customto give a yellow solid which
  5. customwas triturated with ether (3×10 ml)
  6. filtrationThe resulting solid was collected by filtration
  7. customdried in vacuo at 60° C.

Sources & evidence

ORD record
ord-364f3dc09c44428f8fd4d93ad2bd237e
Source dataset
uspto-grants-2005_05
Patent number
US06900216B2

Reaction notes

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