Ethanol → HCID 22474222, compound

HRID 2183665Notes

Reaction equation

HRID 2183665 reaction equation
[Br:1][CH:2](C)[C:3]([C:5]1[S:9][C:8]2[CH:10]=[CH:11][C:12]([F:14])=[CH:13][C:7]=2[CH:6]=1)=O.[NH:16]1[CH2:20][CH2:19][NH:18][C:17]1=[S:21].[CH2:22](O)C>C(O)(=O)C>[BrH:1].[F:14][C:12]1[CH:11]=[CH:10][C:8]2[S:9][C:5]([C:3]3([CH3:2])[CH2:22][S:21][C:17]4=[N:18][CH2:19][CH2:20][N:16]34)=[CH:6][C:7]=2[CH:13]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 2723650EthylenethioureaHCID 22474301HCID 22474301, compound

Product 1

HCID 22474222HCID 22474222, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 2-bromo-1-(5-fluorobenzo[b]thiophen-2-yl)propan-1-one (0.2 g), 2-imidazolidinethione (0.08 g) and ethanol (6 ml) was heated under reflux for 10 minutes. Acetic acid (3 ml) was added, the mixture was heated under reflux for 24 hours, then the solvents were removed in vacuo. Ethanol (10 ml) was added then removed in vacuo, and the residue was dried in vacuo at 60° C. to give 3-(5-fluorobenzo[b]thiophen-2-yl)-3-methyl-5,6-dihydroimidazo[2,1-b]thiazole hydrobromide (0.2 g) as an off-white solid, 1H-nmr (DMSO-d6): δH 2.43 (3H, s, —CH3), 4.22-4.51 (4H, m, —CH2CH2—), 7.36-7.44 (1H, m, ArH), 7.79 (1H, s, ArH), 7.81 (1H, dd, J 9.6 Hz, 2.5 Hz, ArH), 8.13-8.19 (1H, m ArH), 9.3-9.9 (1H, br, H+).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 10 minutes
  3. temperaturethe mixture was heated
  4. temperatureunder reflux for 24 hours
  5. customthe solvents were removed in vacuo
  6. additionEthanol (10 ml) was added
  7. customthen removed in vacuo
  8. customthe residue was dried in vacuo at 60° C.

Sources & evidence

ORD record
ord-7c727c53aa104b0fbfcbd71ae142ec79
Source dataset
uspto-grants-2005_05
Patent number
US06900216B2

Reaction notes

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