Hydrazine hydrate (1:1) → N'-amino-5-methylsulfanyl-4-(4-phenyl-1,3-thiazol-2-yl)thiophene-2-carboximidamide

HRID 2298594

반응식

HRID 2298594 반응식
[CH3:1][S:2][C:3]1[S:7][C:6]([C:8]#[N:9])=[CH:5][C:4]=1[C:10]1[S:11][CH:12]=[C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:14]=1.O.[NH2:22][NH2:23]>CCO>[NH:22]([C:8]([C:6]1[S:7][C:3]([S:2][CH3:1])=[C:4]([C:10]2[S:11][CH:12]=[C:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[N:14]=2)[CH:5]=1)=[NH:9])[NH2:23]

참가 물질

4

반응물 2

HCID 24654Hydrazine hydrate (1:1)HCID 185372645-Methylthio-4-(4-phenyl(1,3-thiazol-2-yl))thiophene-2-carbonitrile

생성물 1

HCID 178503641N'-amino-5-methylsulfanyl-4-(4-phenyl-1,3-thiazol-2-yl)thiophene-2-carboximidamide수율 45%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

5-Methylthio-4-(4-phenyl(1,3-thiazol-2-yl))thiophene-2-carbonitrile (100 mg, 0.32 mmol) as prepared in previous step was dissolved in EtOH (10 mL). To this solution hydrazine monohydrate (10 eq) was added and the mixture was heated at reflux for 3 h. The EtOH solution was concentrated down to 1 mL and water (2 mL) was added to this solution. This resulted in the formation of a white solid. The solid was collected by filtration washed with a small amount of water and dried under vacuum to give 50 mg (45%) of hydrazino[5-methylthio-4-(4-phenyl(1,3-thiazol-2-yl))(2-thienyl)]methanimine. 1H-NMR (CD3OD/CDCl3; 300 MHz) δ2.69 (s, 3H), 7.35-7.43 (m, 1H), 7.44-7.49 (m, 2H), 7.52 (s, 1H), 7.96-7.99 (m, 2), 8.10 (s, 1H). Mass spectrum (ESI, m/z): Calcd. for C15H14N4S3, 347.04 (M+H), found 347.1.

후처리

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 3 h
  3. concentrationThe EtOH solution was concentrated down to 1 mL and water (2 mL)
  4. additionwas added to this solution
  5. customThis resulted in the formation of a white solid
  6. filtrationThe solid was collected by filtration
  7. washwashed with a small amount of water
  8. customdried under vacuum

출처 및 근거

ORD 기록
ord-e66313bc1edc41408ca961bb42437c08
출처 데이터셋
uspto-grants-2002_12
특허 번호
US06492403B1

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