3-Methyl-2-butanone → 4-isopropyl-N-(3-methylbutyl)-1,3-thiazol-2-amine

HRID 2422270

반응식

HRID 2422270 반응식
[CH3:1][CH:2]([CH3:6])[C:3](=O)[CH3:4].BrBr.[CH3:9][CH:10]([CH3:17])[CH2:11][CH2:12][NH:13][C:14]([NH2:16])=[S:15].C([O-])(=O)C.[Na+]>CO>[CH:2]([C:3]1[N:16]=[C:14]([NH:13][CH2:12][CH2:11][CH:10]([CH3:17])[CH3:9])[S:15][CH:4]=1)([CH3:6])[CH3:1]

참가 물질

6

반응물 4

HCID 112513-Methyl-2-butanoneHCID 24408BromineHCID 517045Sodium AcetateHCID 2459097(3-Methyl-butyl)-thiourea

생성물 1

HCID 230830994-isopropyl-N-(3-methylbutyl)-1,3-thiazol-2-amine수율 21.2%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

A solution of 3-methyl-2-butanone (2.64 g) in methanol (30 ml) was cooled to −30° C. bromine (4.8 g) was added, and heated to room temperature with stirring. To the obtained colorless solution were added N-(3-methylbutyl)thiourea (2.92 g) and sodium acetate (2.40 g) and the mixture was stirred with heating under reflux for 2 hrs. The reaction mixture was concentrated, diluted with ethyl acetate and washed with water. The ethyl acetate layer was concentrated, and the residue was purified by silica gel column chromatography with ethyl acetate-hexane (gradient of 1:9 to 2:1 by volume ratio) to give the title compound (0.90 g, yield 21%) as a yellow oil.

후처리

  1. additionwas added
  2. stirringthe mixture was stirred
  3. temperaturewith heating
  4. temperatureunder reflux for 2 hrs
  5. concentrationThe reaction mixture was concentrated
  6. additiondiluted with ethyl acetate
  7. washwashed with water
  8. concentrationThe ethyl acetate layer was concentrated
  9. customthe residue was purified by silica gel column chromatography with ethyl acetate-hexane (gradient of 1:9 to 2:1 by volume ratio)

출처 및 근거

ORD 기록
ord-3e3b63acf6a647f381eb1d9d24bf8573
출처 데이터셋
uspto-grants-2011_06
특허 번호
US07960369B2

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