Stannous Chloride → HCID 21952754, 화합물

HRID 735209

반응식

HRID 735209 반응식
[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]

참가 물질

7

반응물 3

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

생성물 1

HCID 21952754HCID 21952754, 화합물수율 93%

시약·촉매·용매 3

HCID 313Hydrochloric Acid용매2회HCID 962Water용매HCID 6422Trifluoroacetic acid용매

반응 조건

온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-cc0a247dadd8430aaa2400a068bb8295
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07592454B2

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