Acetic Acid → HCID 22474239, compound

HRID 2183638Notes

Reaction equation

HRID 2183638 reaction equation
[Br:1][CH:2]([CH3:15])[C:3]([C:5]1[S:9][C:8]2[CH:10]=[CH:11][CH:12]=[C:13]([CH3:14])[C:7]=2[CH:6]=1)=O.[NH:16]1[CH2:20][CH2:19][NH:18][C:17]1=[S:21].C(O)(=O)C>C(O)C>[BrH:1].[CH3:15][C:2]1[S:21][C:17]2=[N:16][CH2:20][CH2:19][N:18]2[C:3]=1[C:5]1[S:9][C:8]2[CH:10]=[CH:11][CH:12]=[C:13]([CH3:14])[C:7]=2[CH:6]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 2723650EthylenethioureaHCID 22473879HCID 22473879, compound

Product 1

HCID 22474239HCID 22474239, compoundYield 85.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-bromo-1-(4-methylbenzo[b]thiophen-2-yl)propan-1-one (0.27 g), 2-imidazolidinethione (0.1 g), acetic acid (2 ml) and ethanol (4 ml) was heated under reflux for 3 hours, then cooled to ambient temperature. The solvents were removed in vacuo and the residue was triturated with ether (2×1 ml). The resulting solid was collected by filtration, washed with ethanol (2 ml) and dried in vacuo at 60° C. for 2 hours to give 2-methyl-3-(4-methylbenzo[b]thiophen-2-yl)-5,6-dihydroimidazo[2,1-b]thiazole hydrobromide (0.3 g) as a cream solid, m.p. 201-204° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 3 hours
  3. customThe solvents were removed in vacuo
  4. customthe residue was triturated with ether (2×1 ml)
  5. filtrationThe resulting solid was collected by filtration
  6. washwashed with ethanol (2 ml)
  7. customdried in vacuo at 60° C. for 2 hours

Sources & evidence

ORD record
ord-ba79f3cb39544003ab4dd827f218eb3e
Source dataset
uspto-grants-2005_05
Patent number
US06900216B2

Reaction notes

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