Methyl iodide → 2-(Methylsulfanyl)[1,2,4]triazino[1,6-a]indol-4(1H)-one

HRID 1261973Notes

Reaction equation

[S:1]=[C:2]1[NH:14][C:13](=[O:15])[C:5]2=[CH:6][C:7]3[C:12]([N:4]2[NH:3]1)=[CH:11][CH:10]=[CH:9][CH:8]=3.CI.[C:18]([O-])(O)=O.[Na+]>O1CCCC1>[CH3:18][S:1][C:2]1[NH:14][C:13](=[O:15])[C:5]2=[CH:6][C:7]3[C:12]([N:4]2[N:3]=1)=[CH:11][CH:10]=[CH:9][CH:8]=3

Participants

Conditions

Temperature: 45 °C

Procedure

Into a round-bottom flask 2-thioxo-2,3-dihydro-1H-[1,2,4]triazino[1,6-a]indol-4-one (9.25 g, 0.04 mol) and methyl iodide (3.42 mL, 0.0549 mol) were combined in tetrahydrofuran (200 mL). The reaction was stirred at 45° C. for one hour. The solvent was removed under vacuum to give a solid, which was next stirred for 30 minutes with saturated aqueous NaHCO3 (100 mL). The solid was filtered and washed with water, then dried on high vacuum and further by azeotrop distillation with toluene to give 2-methylsulfanyl-3H-[1,2,4]triazino[1,6-a]indol-4-one (7 g, 71%), which was used in the next step without further purification. 1H-NMR (DMSO-d6) δ 12.28 (br s, 1H), 7.87 (d, J=8.4 Hz, 1H), 7.80 (d, J=8.1 Hz, 1H), 7.43 (m, 1H), 7.28 (m, 1H), 7.18 (s, 1H), 2.64 (s, 3H).

Workup

customThe solvent was removed under vacuum
customto give a solid, which
filtrationThe solid was filtered
washwashed with water
dry with materialdried on high vacuum and further by azeotrop distillation with toluene

Sources & evidence

ORD record: ord-0d83248fc77046d2ae3f0f638cc252ea
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08471005B2

Reaction notes

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