Ethanol → HCID 21258456, compound

HRID 635361Notes

Reaction equation

HRID 635361 reaction equation
[Br:1][CH:2]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:3]([C:5]1([C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[C:11]([Cl:16])[CH:10]=2)[CH2:8][CH2:7][CH2:6]1)=O.[NH:23]1[CH2:27][CH2:26][NH:25][C:24]1=[S:28].C(O)C>C(O)(=O)C>[BrH:1].[Cl:16][C:11]1[CH:10]=[C:9]([C:5]2([C:3]3[N:25]4[CH2:26][CH2:27][N:23]=[C:24]4[S:28][C:2]=3[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:8][CH2:7][CH2:6]2)[CH:14]=[CH:13][C:12]=1[Cl:15]

Participants

5

Reactant 3

HCID 702EthanolHCID 2723650EthylenethioureaHCID 21258424HCID 21258424, compound

Product 1

HCID 21258456HCID 21258456, compoundYield 31.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 2-bromo-1-[1-(3,4-dichlorophenyl)cyclobutyl]-2-phenylethanone (3.8 g), imidazolidine-2-thione (0.97 g), ethanol (70 ml) and acetic acid (40 ml) was heated under reflux for 20 hours then allowed to cool to ambient temperature. The solvents were removed in vacuo and the residue was crystallised from ethanol. The resulting product was collected by filtration, washed with ethanol (10 ml) and dried in vacuo at 100° C. to give 3-[1-(3,4-dichlorophenyl)cyclobutyl]-2-phenyl-5,6-dihydroimidazo[2,1-b]thiazole hydrobromide as a pale brown solid (1.43 g), m.p. 280° C. (decomposes).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 20 hours
  3. customThe solvents were removed in vacuo
  4. customthe residue was crystallised from ethanol
  5. filtrationThe resulting product was collected by filtration
  6. washwashed with ethanol (10 ml)
  7. customdried in vacuo at 100° C.

Sources & evidence

ORD record
ord-013baa0ec7cd4033952dc5f03b94c054
Source dataset
uspto-grants-2001_02
Patent number
US06187802B1

Reaction notes

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