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Ethanethiol → 3,6-Dihydro-4-methyl-6-(3-nitrophenyl)-2-thioxo-1,5(2H)-pyrimidinedicarboxylic acid, 1-methyl 5-(1-methylethyl) ester

HRID 1590289
ノート
印刷プレビュー

反応式

HRID 1590289 の反応式
F[C:2](F)(F)[C:3]([OH:5])=[O:4].[CH2:8](S)[CH3:9].C[C:12]1[NH:13][C:14](=[S:33])[N:15](C(O)=O)[CH:16]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([N+:27]([O-:29])=[O:28])[CH:22]=2)[C:17]=1C(O)=O.[C:34]([O:37][CH2:38]C)(=[O:36])C.Cl[CH2:41]Cl>>[CH3:17][C:12]1[NH:13][C:14](=[S:33])[N:15]([C:34]([O:37][CH3:38])=[O:36])[CH:16]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([N+:27]([O-:29])=[O:28])[CH:22]=2)[C:2]=1[C:3]([O:5][CH:8]([CH3:9])[CH3:41])=[O:4]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 5

HCID 6343EthanethiolHCID 6344Dichloromethane2 回HCID 6422Trifluoroacetic acidHCID 8857Ethyl AcetateHCID 197695663,6-dihydro-4-methyl-6-(3-nitrophenyl)-2-thioxo-1,5(2H)-pyrimidinedicarboxylic acid

生成物 1

HCID 71722732
3,6-Dihydro-4-methyl-6-(3-nitrophenyl)-2-thioxo-1,5(2H)-pyrimidinedicarboxylic acid, 1-methyl 5-(1-methylethyl) ester

実験手順

The ester product from part (b) (7.42 g.) is dissolved in dichloromethane (50 ml.) and treated with trifluoroacetic acid (5 ml.) and ethanethiol (1.5 ml.). The reaction is stirred at room temperature for 16 hours, and then dichloromethane (50 ml.) is added. The organic layer is washed with water (2×150 ml.), saturated sodium bicarbonate (2×150 ml.), saturated sodium carbonate (100 ml.), sodium dihydrogen phosphate (100 ml.), and saturated sodium chloride (100 ml.), dreid over magnesium sulfate, and evaporated in vacuo to give 6.31 g. of product as an oil. Crystallization from ethyl acetate: hexanes gives 3.2 g. of yellow solid 3,6-dihydro-4-methyl-6-(3-nitrophenyl)-2-thioxo-1,5(2H)-pyrimidinedicarboxylic acid, 5-(1-methylethyl 1-methyl ester; m.p. 130.5°-131.5°. TLC (silica gel; ethyl acetate:hexanes, 1:2) Rf =0.30.

後処理

  1. washThe organic layer is washed with water (2×150 ml.), saturated sodium bicarbonate (2×150 ml.), saturated sodium carbonate (100 ml.), sodium dihydrogen phosphate (100 ml.), and saturated sodium chloride (100 ml.)
  2. customevaporated in vacuo
  3. customto give 6.31 g
  4. customCrystallization from ethyl acetate
  5. customhexanes gives 3.2 g

出典と根拠

ORDレコード
ord-871afc86ff534278bd57dd380c761dbd
出典データセット
uspto-grants-1993_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05202330

反応ノート

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