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

HRID 908630ノート

反応式

HRID 908630 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-4c3ca7b09f8d428e9208b2aef89a2616
出典データセット
uspto-grants-2011_09
特許番号
US08017612B2

反応ノート

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