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

HRID 590510Notes

Reaction equation

[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]

Participants

Conditions

Temperature: 25 °C

Procedure

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+).

Workup

dissolutiondissolved
customprecipitated out
filtrationThis was filtered off
washwashed with water
customdried in vacuo

Sources & evidence

ORD record: ord-eeb75717be924d1bb28a7c82da3e4b5f
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09233982B2

Reaction notes

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