Sodium Hydroxide → 5',6,6',7-tetrahydro-5H-spiro[benzo[b]thiophene-4,4'-[1,3]thiazin]-2'-amine

HRID 590510노트

반응식

HRID 590510 반응식
[C:1]([S:4][CH2:5][CH:6]=[C:7]1[C:15]2[CH:14]=[CH:13][S:12][C:11]=2[CH2:10][CH2:9][CH2:8]1)(=[NH:3])[NH2:2].[OH-].[Na+]>Cl>[S:4]1[CH2:5][CH2:6][C:7]2([C:15]3[CH:14]=[CH:13][S:12][C:11]=3[CH2:10][CH2:9][CH2:8]2)[N:3]=[C:1]1[NH2:2]

참가 물질

4

반응물 2

HCID 14798Sodium HydroxideHCID 1232787902-(6,7-dihydrobenzo[b]thiophen-4(5H)-ylidene)ethyl carbamimidothioate

생성물 1

HCID 900705375',6,6',7-tetrahydro-5H-spiro[benzo[b]thiophene-4,4'-[1,3]thiazin]-2'-amine수율 94.4%

시약·촉매·용매 1

HCID 313Hydrochloric Acid용매

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온도
25 °C

실험 절차

2-(6,7-Dihydrobenzo[b]thiophen-4(5H)-ylidene)ethyl carbamimidothioate (13.8 g, 46 mmol) was suspended in concentrated HCl (150 mL) and stirred at 25° C. until all the solid dissolved. The reaction was monitored by LC/MS until no more starting material remained. The mixture was then neutralised with aqueous 2 M NaOH solution and ice whereupon a solid precipitated out. This was filtered off, washed with water and dried in vacuo to yield the title compound as a white solid (10.35 g, 93%). 1H NMR δ (ppm)(CHCl3-d): 7.05 (1H, d, J=5.25 Hz), 6.88 (1H, d, J=5.24 Hz), 4.79 (2H, s), 3.20-3.01 (2H, m), 2.90-2.74 (2H, m), 2.10-1.98 (2H, m), 1.96-1.77 (4H, m). LCMS (Method f) Rt 2.83 (min) m/z 239 (MH+).

후처리

  1. dissolutiondissolved
  2. customprecipitated out
  3. filtrationThis was filtered off
  4. washwashed with water
  5. customdried in vacuo

출처 및 근거

ORD 기록
ord-eeb75717be924d1bb28a7c82da3e4b5f
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09233982B2

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