Methylamine → HCID 46932331, compound

HRID 1192073Notes

Reaction equation

S(Cl)(Cl)=O.[Cl:5][C:6]1[C:11]([Cl:12])=[CH:10][CH:9]=[CH:8][C:7]=1[S:13][C:14]1[S:18][C:17]([C:19](O)=[O:20])=[CH:16][C:15]=1[N+:22]([O-:24])=[O:23].[CH3:25][NH2:26]>C1(C)C=CC=CC=1.O1CCOCC1>[Cl:5][C:6]1[C:11]([Cl:12])=[CH:10][CH:9]=[CH:8][C:7]=1[S:13][C:14]1[S:18][C:17]([C:19]([NH:26][CH3:25])=[O:20])=[CH:16][C:15]=1[N+:22]([O-:24])=[O:23]

Participants

Conditions

Temperature: 80 °C

Procedure

Thionyl chloride (0.102 g, 0.86 mmol) was added to a suspension of 5-(2,3-dichlorophenylsulfanyl)-4-nitrothiophene-2-carboxylic acid (0.15 g, 0.43 mmol) in toluene (5 mL) and the stirred mixture was heated at 80° C. for 1 hour. TLC analysis showed no acid remaining so the mixture was allowed to cool to ambient temperature and then concentrated in vacuo to give the dark brown viscous oil. The oil was dissolved in 1,4-dioxane (1 mL) and added at 5° C. to stirred 40% aqueous methylamine solution (5 mL). The mixture was stirred for 15 minutes then the resulting solid was collected by filtration, washed with water (3×1 mL) and dried in vacuo at 40° C. overnight to afford the title product as a beige solid (55 mg, 35% yield). 1H NMR (CDCl3) δ: 7.84 (1H, s) 7.70 (2H, m), 7.36 (1H, m), 6.01 (1H, broad s), 2.95 (3H, d, J=4.9 Hz).

Workup

temperatureto cool to ambient temperature
concentrationconcentrated in vacuo
customto give the dark brown viscous oil
additionadded at 5° C.
filtrationthe resulting solid was collected by filtration
washwashed with water (3×1 mL)
customdried in vacuo at 40° C. overnight

Sources & evidence

ORD record: ord-a136f52e830e45f294b6f53cf79a5bcf
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08680139B2

Reaction notes

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