Sodium methanethiolate → HCID 178456950, compound

HRID 482283Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[C:4]([Cl:9])[C:3]=1[N:10]1[N:15]=[C:14]([N:16]([CH:20]([CH:24]2[CH2:26][CH2:25]2)[CH:21]2[CH2:23][CH2:22]2)[CH2:17][CH2:18][CH3:19])[CH:13]=[C:12](Cl)[NH:11]1.[CH3:28][S-:29].[Na+].C(OCC)(=O)C.O>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[C:4]([Cl:9])[C:3]=1[N:10]1[N:15]=[C:14]([N:16]([CH:20]([CH:24]2[CH2:26][CH2:25]2)[CH:21]2[CH2:23][CH2:22]2)[CH2:17][CH2:18][CH3:19])[CH:13]=[C:12]([S:29][CH3:28])[NH:11]1

Participants

Conditions

Temperature: 23 °C

Procedure

A solution of 2-(2',4',6'-trichlorophenyl)-4-(N-dicyclopropylmethyl-N-propylamino)-6-chlorotriazine (130 mg, 0.3 mmole) in 2.5 mL of dimethylformamide was treated with sodium thiomethylate (0.04 mg, 0.57 mmole) with stirring at 23° C. for 1 hour, the mixture was then poured into ethyl acetate/water. The organic phase was washed with water, 0.1M aqueous hydrochloric acid and brine, dried over magnesium sulfate and concentrated. The residue was purified by preparative TLC (5% diethyl ether/hexane) to give 2-(2',4',6'-trichlorophenyl)-4-(N-dicyclopropylmethyl-N-propylamino)-6-methylthiotriazin (110 mg, 80% yield). 1H NMR (CDCl3): 0.2-0.7 (bm, 8H), 0.7-1.2 (bm, 5H), 1.7-1.8 (bm, 2H), 2.3-2.6 (m, 3H), 3.2-3.5 (bm, 3H), 4.8-5.1 (bm, 2H), 7.35 (5, 1H) and 7.38 (s, 1H). Mass (ion spray): 457 (M+H).

Workup

washThe organic phase was washed with water, 0.1M aqueous hydrochloric acid and brine
dry with materialdried over magnesium sulfate
concentrationconcentrated
customThe residue was purified by preparative TLC (5% diethyl ether/hexane)

Sources & evidence

ORD record: ord-042d6cacc2f04885a945d854a9d4eeef
Source dataset: uspto-grants-1998_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05795905

Reaction notes

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