Carbon Dioxide → Imidazo[5,1-B]thiazole-7-carboxylic acid

HRID 1839307노트

반응식

HRID 1839307 반응식
C([Mg]Br)C.C1COCC1.I[C:11]1[N:12]=[CH:13][N:14]2[CH:18]=[CH:17][S:16][C:15]=12.[C:19](=[O:21])=[O:20].[OH-].[Na+]>C1COCC1.CCOCC>[S:16]1[CH:17]=[CH:18][N:14]2[CH:13]=[N:12][C:11]([C:19]([OH:21])=[O:20])=[C:15]12

참가 물질

7

반응물 4

HCID 280Carbon DioxideHCID 14798Sodium HydroxideHCID 177737777-Iodoimidazo[5,1-B]thiazoleHCID 178420660HCID 178420660, 화합물

생성물 1

HCID 23449010Imidazo[5,1-B]thiazole-7-carboxylic acid수율 83.7%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매

실험 절차

A 0.95 M ethylmagnesium bromide/THF solution (12.6 ml) was added dropwise to a solution (50 ml) of 2.501 g of 7-iodoimidazo[5,1-b]thiazole in THF ac −70° C. The mixture was stirred for 30 min. Carbon dioxide (which had been evolved from about 5 g of dry ice and passed through a calcium chloride tube) was introduced into the reaction solution at the same temperature over a period of 40 min. The reaction solution was allowed to stand at −20° C. overnight, and then added to an ice cold mixed solution composed of an aqueous sodium hydroxide (0.41 g) solution (100 ml) and ether (200 ml) with stirring. The mixture was stirred for one hr. The organic layer was separated and concentrated under the reduced pressure by a minor amount, and the remaining organic solvent was removed by distillation. The residue was adjusted to pH 3.5 by the addition of 2 N hydrochloric acid under ice cooling. The resultant precipitate was washed with a minor amount of cold water, and then dried under the reduced pressure to give 1.407 g of imidazo[5,1-b]thiazole-7-carboxylic acid.

후처리

  1. waitto stand at −20° C. overnight
  2. stirringwith stirring
  3. stirringThe mixture was stirred for one hr
  4. customThe organic layer was separated
  5. concentrationconcentrated under the reduced pressure by a minor amount
  6. customthe remaining organic solvent was removed by distillation
  7. additionThe residue was adjusted to pH 3.5 by the addition of 2 N hydrochloric acid under ice cooling
  8. washThe resultant precipitate was washed with a minor amount of cold water
  9. customdried under the reduced pressure

출처 및 근거

ORD 기록
ord-187cacda99a34f9c8bfe16d1f1bca878
출처 데이터셋
uspto-grants-2004_01
특허 번호
US06677331B2

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