Ethanol → HCID 22473804, compound

HRID 2183639Notes

Reaction equation

HRID 2183639 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]([Cl:14])[C:7]=2[CH:6]=1)=O.[N:16]1[CH2:21][CH2:20][CH2:19][NH:18][C:17]=1[SH: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:18]4[CH2:19][CH2:20][CH2:21][N:16]=[C:17]4[S:22][C:2]=3[CH3:15])[S:9][C:8]=2[CH:10]=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 22474281HCID 22474281, compoundHCID 178527864HCID 178527864, compound

Product 1

HCID 22473804HCID 22473804, compoundYield 40.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
95 °C

Procedure

A mixture of 2-bromo-1-(4-chlorobenzo[b]thiophen-2-yl)propan-1-one (0.5 g), 3,4,5,6-tetrahydro-2-pyrimidinethiol (0.144 g) and ethanol (8 ml) was heated under reflux for 20 minutes. Acetic acid (4 ml) was added, the mixture was heated under reflux for 18 hours then the solvents were removed in vacuo. 2.5M Sulphuric acid (10 ml) was added, the mixture was heated at 95° C. for 4.5 hours, then water (30 ml) was added and the mixture was basified to pH 7 by the addition of 5M aqueous sodium hydroxide solution. The product was extracted into dichloromethane (3×25 ml), the combined extracts were dried (MgSO4), and the solvent was removed in vacuo. The residue was dissolved in ethanol (20 ml) and hydrogen bromide (30% solution in acetic acid; 0.5 ml) was added. The solution was added dropwise to stirred ether (50 ml) and the resulting solid was collected by filtration and recrystallised from propan-2-ol (35 ml) to give 3-(4-chlorobenzo[b]thiophen-2-yl)-2-methyl-6,7-dihydro-5H-thiazolo[3,2-a]pyrimidine hydrobromide (0.2 g) as a white solid, m.p. 236-238° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 20 minutes
  3. temperaturethe mixture was heated
  4. temperatureunder reflux for 18 hours
  5. customthe solvents were removed in vacuo
  6. addition2.5M Sulphuric acid (10 ml) was added
  7. additionwater (30 ml) was added
  8. additionthe mixture was basified to pH 7 by the addition of 5M aqueous sodium hydroxide solution
  9. extractionThe product was extracted into dichloromethane (3×25 ml)
  10. dry with materialthe combined extracts were dried (MgSO4)
  11. customthe solvent was removed in vacuo
  12. dissolutionThe residue was dissolved in ethanol (20 ml)
  13. additionhydrogen bromide (30% solution in acetic acid; 0.5 ml) was added
  14. additionThe solution was added dropwise
  15. filtrationthe resulting solid was collected by filtration
  16. customrecrystallised from propan-2-ol (35 ml)

Sources & evidence

ORD record
ord-f9be6c007c894f59b60ce39ee4f4177b
Source dataset
uspto-grants-2005_05
Patent number
US06900216B2

Reaction notes

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