Ethanol → HCID 22473804, 화합물

HRID 2183639노트

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HRID 2183639 반응식
[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

참가 물질

5

반응물 3

HCID 702EthanolHCID 22474281HCID 22474281, 화합물HCID 178527864HCID 178527864, 화합물

생성물 1

HCID 22473804HCID 22473804, 화합물수율 40.2%

시약·촉매·용매 1

HCID 176Acetic Acid용매

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온도
95 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-f9be6c007c894f59b60ce39ee4f4177b
출처 데이터셋
uspto-grants-2005_05
특허 번호
US06900216B2

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