Methylamine → HCID 46932239, compound

HRID 1192056Notes

Reaction equation

HRID 1192056 reaction equation
Br[CH:2]([C:4]1[S:8][C:7]([S:9][C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=2[Cl:17])=[C:6]([N+:18]([O-:20])=[O:19])[CH:5]=1)[CH3:3].[CH3:21][NH2:22]>O1CCCC1>[Cl:17][C:11]1[CH:12]=[C:13]([Cl:16])[CH:14]=[CH:15][C:10]=1[S:9][C:7]1[S:8][C:4]([CH:2]([NH:22][CH3:21])[CH3:3])=[CH:5][C:6]=1[N+:18]([O-:20])=[O:19]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 60207313HCID 60207313, compound

Product 1

HCID 46932239HCID 46932239, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 5-(1-bromoethyl)-2-(2,4-dichlorophenyl)sulfanyl-3-nitro-thiophene (0.1 g, 0.243 mmol) in tetrahydrofuran (5 mL), was added N-methylamine (0.012 mL, 0.29 mmol). The resulting reaction mixture was heated at 80° C. under microwave irradiation (200 W) on a CEM Discovery™ microwave machine for 50 minutes. The reaction mixture was concentrated and the crude was purified by silica gel chromatography to afford the title compound as a yellow solid (30 mg, 33% yield). 1H NMR (400 MHz, d6-DMSO) δ: 7.83 (2H, m), 7.54 (1H, m), 7.49 (1H, s), 3.83 (1H, q), 2.44 (3H, s), 1.32 (3H, d). MS m/z: 376.8 [M+H]+.

Workup

  1. customThe resulting reaction mixture
  2. concentrationThe reaction mixture was concentrated
  3. customthe crude was purified by silica gel chromatography

Sources & evidence

ORD record
ord-ef34ca2e554541f3a576b5bc196f3b50
Source dataset
uspto-grants-2014_03
Patent number
US08680139B2

Reaction notes

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