Stannous Chloride → HCID 21952754、化合物

HRID 735209

反応式

HRID 735209 の反応式
[CH3:1][S:2][C:3]1[CH:9]=[CH:8][CH:7]=[CH:6][C:4]=1[NH2:5].[N:10]([O-])=O.[Na+].[Sn](Cl)[Cl:15]>Cl.FC(F)(F)C(O)=O.O>[ClH:15].[CH3:1][S:2][C:3]1[CH:9]=[CH:8][CH:7]=[CH:6][C:4]=1[NH:5][NH2:10]

参加物

7

反応物 3

HCID 24479Stannous ChlorideHCID 763372-(Methylthio)anilineHCID 23668193Sodium Nitrite

生成物 1

HCID 21952754HCID 21952754、化合物収率 93%

試薬・触媒・溶媒 3

HCID 313Hydrochloric Acid溶媒2 回HCID 962Water溶媒HCID 6422Trifluoroacetic acid溶媒

反応条件

温度
0 °C

実験手順

2-(Methylmercapto)aniline (23.6 g, 169.5 mmol) was suspended in conc. HCl (200 mL) and trifluoroacetic acid (130 mL), and cooled to 0° C. in an ice bath. Sodium nitrite (14.0 g, 203.4 mmol) was dissolved in water (45 mL) and added dropwise to the suspension over 45 minutes. After the addition, the reaction was stirred at 0° C. for 1 h. In a separate flask, tin (II) chloride (76 g, 338.4 mmol) was dissolved in conc. HCl (100 mL) and added slowly over 15 minutes to the reaction mixture. The resultant suspension was warmed to room temperature and stirred for 48 hours. The reaction was filtered, washed with isopropyl alcohol (15 mL), and dried to give 1-[2-(methylsulfanyl)phenyl]hydrazine hydrochloride (30 g, 93%). 1H NMR (CD3OD, 300 MHz) δ 7.44 (d, 1H, J=7.7 Hz), 7.32-7.26 (m, 1H), 7.08-7.00 (m, 2H), 2.39 (s, 3H) ppm.

後処理

  1. additionadded dropwise to the suspension over 45 minutes
  2. additionAfter the addition
  3. additionadded slowly over 15 minutes to the reaction mixture
  4. stirringstirred for 48 hours
  5. filtrationThe reaction was filtered
  6. washwashed with isopropyl alcohol (15 mL)
  7. customdried

出典と根拠

ORDレコード
ord-cc0a247dadd8430aaa2400a068bb8295
出典データセット
uspto-grants-2009_09
特許番号
US07592454B2

関連ノート

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