Thiourea → Methyl 2-amino-4-(methoxymethyl)thiazole-5-carboxylate

HRID 908630노트

반응식

HRID 908630 반응식
[CH3:1][O:2][C:3](=[O:11])[CH:4](Br)[C:5](=O)[CH2:6][O:7][CH3:8].[NH2:12][C:13]([NH2:15])=[S:14]>C(O)C>[CH3:1][O:2][C:3]([C:4]1[S:14][C:13]([NH2:15])=[N:12][C:5]=1[CH2:6][O:7][CH3:8])=[O:11]

참가 물질

4

반응물 2

HCID 2723790ThioureaHCID 53423683Methyl 2-bromo-4-methoxy-3-oxobutanoate

생성물 1

HCID 25220423Methyl 2-amino-4-(methoxymethyl)thiazole-5-carboxylate수율 54%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A solution of the crude product (about 30 mmol) obtained in Step 1 and thiourea (2.28 g) in ethanol (60 ml) was heated under reflux overnight. After cooling to room temperature, the reaction mixture was partitioned by adding ethyl acetate and water. The organic layer was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate, filtrated, and concentrated under reduced pressure. Then, suitable amounts of isopropanol, chloroform, ethyl acetate and diisopropyl ether were added, and the mixture was stirred at room temperature for 30 min. The precipitated crystals were collected by filtration and dried to give the title compound (3.27 g).

후처리

  1. temperatureunder reflux overnight
  2. customthe reaction mixture was partitioned
  3. additionby adding ethyl acetate and water
  4. washThe organic layer was washed successively with water and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltrated
  7. concentrationconcentrated under reduced pressure
  8. additionThen, suitable amounts of isopropanol, chloroform, ethyl acetate and diisopropyl ether were added
  9. filtrationThe precipitated crystals were collected by filtration
  10. customdried

출처 및 근거

ORD 기록
ord-4c3ca7b09f8d428e9208b2aef89a2616
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08017612B2

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