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

HRID 2298594

反応式

HRID 2298594 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-e66313bc1edc41408ca961bb42437c08
出典データセット
uspto-grants-2002_12
特許番号
US06492403B1

関連ノート

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