Sulfuric Acid → 6-Amino-1-[2-(1H-benzimidazol-2-yl)ethyl]-2-thioxo-2,3-dihydropyrimidin-4(1H)-one

HRID 912679

반응식

HRID 912679 반응식
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH2:10][CH2:11][NH:12][C:13]([NH2:15])=[S:14].[O-]CC.[Na+].[C:20]([CH2:22][C:23](OCC)=[O:24])#[N:21].S(=O)(=O)(O)O>C(O)C.O>[NH2:21][C:20]1[N:12]([CH2:11][CH2:10][C:2]2[NH:3][C:4]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=3[N:1]=2)[C:13](=[S:14])[NH:15][C:23](=[O:24])[CH:22]=1

참가 물질

7

반응물 4

HCID 1118Sulfuric AcidHCID 7764Ethyl cyanoacetateHCID 2723922Sodium ethoxideHCID 391501851-[2-(1H-Benzimidazol-2-yl)ethyl]thiourea

생성물 1

HCID 730143156-Amino-1-[2-(1H-benzimidazol-2-yl)ethyl]-2-thioxo-2,3-dihydropyrimidin-4(1H)-one수율 96%

시약·촉매·용매 2

HCID 702Ethanol용매2회HCID 962Water용매

실험 절차

To a suspension of 1-[2-(1H-benzimidazol-2-yl)ethyl]thiourea (0.44 g, 2.0 mmol, obtained from Example 12(a)) in absolute ethanol (5 mL) at 80° C. were added, over 2 h, a solution of sodium ethoxide (21% w/v, 2.2 mL, 6.0 mmol) and a solution of ethyl cyanoacetate (0.64 mL, 6.0 mmol) in absolute ethanol (1.3 mL). The reaction was kept at 80° C. for an additional 3 h. After cooling to r.t., water (75 mL) was added and the pH adjusted to ˜7 using concentrated sulfuric acid. The solid that formed was collected by filtration, washed with water and dried in vacuo to give the title compound (0.55 g, 96% yield).

후처리

  1. additionwere added, over 2 h
  2. customThe solid that formed
  3. filtrationwas collected by filtration
  4. washwashed with water
  5. customdried in vacuo

출처 및 근거

ORD 기록
ord-01591f346d0e47a7b05f454faf1490ba
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08026244B2

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