Hydrochloric Acid → 6-(2-chloroethyl)-7-methyl-5H-(1,3)thiazolo(3,2-a)pyrimidin-5-one

HRID 484708

反応式

HRID 484708 の反応式
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[NH2:6].[C:7]([CH:10]1[CH2:14][CH2:13][O:12][C:11]1=O)(=O)[CH3:8].Cl.P(Cl)(Cl)([Cl:19])=O>O.CC1C=CC=CC=1>[Cl:19][CH2:13][CH2:14][C:10]1[C:11](=[O:12])[N:3]2[CH:4]=[CH:5][S:1][C:2]2=[N:6][C:7]=1[CH3:8]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 21552-AminothiazoleHCID 106012-AcetylbutyrolactoneHCID 24813Phosphorus oxychloride

生成物 1

HCID 8178726-(2-chloroethyl)-7-methyl-5H-(1,3)thiazolo(3,2-a)pyrimidin-5-one

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 1140Toluene溶媒

実験手順

A mixture of 50 parts of 2-thiazolamine, 76 parts of 3-acetyl-4,5-dihydro-2(3H)-furanone, 1.2 parts of concentrate hydrochloric acid and 270 parts of methylbenzene was stirred and refluxed for 2 hours using a water-separator. The reaction mixture was cooled and 340 parts of phosphoryl chloride were added at a temperature between 20° and 30° C. The whole was heated slowly to 100°-110° C. and stirring was continued for 2 hours at this temperature. The reaction mixture was evaporated and the residue was poured onto a mixture of crushed ice and ammonium hydroxide. The product was extracted with trichloromethane. The extract was dried, filtered and evaporated. The residue was purified by column-chromatography over silica gel using a mixture of trichloromethane and methanol (95:5 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from a mixture of 2-propanol and 1,1'-oxybisethane, yielding 36 parts of 6-(2-chloroethyl)- 7-methyl-5H-thiazolo[3,2-a]pyrimidin-5-one (intermediate 5).

後処理

  1. temperaturerefluxed for 2 hours
  2. temperatureThe reaction mixture was cooled
  3. temperatureThe whole was heated slowly to 100°-110° C.
  4. stirringstirring
  5. customThe reaction mixture was evaporated
  6. additionthe residue was poured onto a mixture of crushed ice and ammonium hydroxide
  7. extractionThe product was extracted with trichloromethane
  8. customThe extract was dried
  9. filtrationfiltered
  10. customevaporated
  11. customThe residue was purified by column-chromatography over silica gel using
  12. additiona mixture of trichloromethane and methanol (95:5 by volume) as eluent
  13. customThe pure fractions were collected
  14. customthe eluent was evaporated
  15. customThe residue was crystallized from a mixture of 2-propanol and 1,1'-oxybisethane

出典と根拠

ORDレコード
ord-6a6bb6747b0f430b8b5d9dff5992a315
出典データセット
uspto-grants-1985_08
特許番号
US04533665

関連ノート

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