Ethyl 2-methylacetoacetate → 5,6-Dimethyl-2-thiouracil

HRID 63093

反応式

HRID 63093 の反応式
CC(C)([O-])C.[K+].[CH3:7][CH:8]([C:14](=O)[CH3:15])[C:9](OCC)=[O:10].[NH2:17][C:18]([NH2:20])=[S:19]>O1CCCC1.C(O)C>[CH3:7][C:8]1[C:9](=[O:10])[NH:17][C:18](=[S:19])[NH:20][C:14]=1[CH3:15]

参加物

6

反応物 3

HCID 701Ethyl 2-methylacetoacetateHCID 2723790ThioureaHCID 23665647Potassium tert-butoxide

生成物 1

HCID 27362495,6-Dimethyl-2-thiouracil収率 78.5%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a stirred solution of potassium tert-butoxide (15.71 g, 0.140 mol) in tetrahydrofuran (200 mL) was added a solution of ethyl 2-methyl-3-oxobutanoate (20.0 g, 0.14 mol) and thiourea (10.55 g, 0.14 mol) in dry ethanol (150 mL). The resulting mixture was refluxed for 15 minutes and cooled down to ambient temperature. The formed precipitate was collected by filtration, washed with tetrahydrofuran (200 mL), and dissolved in water (200 mL). Acetic acid (100 mL) was added in to the resulting solution. The formed precipitate was collected by filtration and dried to yield 17 g (78.5%) of the titled compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.74 (s, 3H) 2.09 (s, 3H) 12.19 (s, 1H).

後処理

  1. temperatureThe resulting mixture was refluxed for 15 minutes
  2. filtrationThe formed precipitate was collected by filtration
  3. washwashed with tetrahydrofuran (200 mL)
  4. dissolutiondissolved in water (200 mL)
  5. additionAcetic acid (100 mL) was added in to the resulting solution
  6. filtrationThe formed precipitate was collected by filtration
  7. customdried

出典と根拠

ORDレコード
ord-e0a657aacced4bb1a486db75d60cc8f0
出典データセット
uspto-grants-2016_09
特許番号
US09447051B2

関連ノート

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