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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
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HRID 1590289 반응식
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]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 5

HCID 6343EthanethiolHCID 6344Dichloromethane2회HCID 6422Trifluoroacetic acidHCID 8857Ethyl AcetateHCID 197695663,6-dihydro-4-methyl-6-(3-nitrophenyl)-2-thioxo-1,5(2H)-pyrimidinedicarboxylic acid

생성물 1

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

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-871afc86ff534278bd57dd380c761dbd
출처 데이터셋
uspto-grants-1993_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05202330

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