Methylamine → HCID 19975707, compound

HRID 1898906Notes

Reaction equation

HRID 1898906 reaction equation
[Br:1][C:2]1[C:6]2[CH:7]=[C:8]([CH2:11]Br)[CH:9]=[CH:10][C:5]=2[O:4][C:3]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[C:19]#[N:20].[CH3:21][NH2:22]>C1COCC1>[Br:1][C:2]1[C:6]2[CH:7]=[C:8]([CH2:11][NH:22][CH3:21])[CH:9]=[CH:10][C:5]=2[O:4][C:3]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[C:19]#[N:20]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 19975734HCID 19975734, compound

Product 1

HCID 19975707HCID 19975707, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3.1 g (7.9 mmol) 3-Bromo-5-(bromomethyl)-2-(2-cyanophenyl)benzofuran (prepared according to EP 434 249) were dissolved in 50 ml THF, and 25 ml of a 40% aqueous solution of methylamine was added via a dropping funnel. The mixture was stirred at room temperature over night and warmed for 2 h at 40° C. The solvent was removed in vacuo, the residue stirred with water, filtrated by suction, and washed with water. The title compound was purified by column chromatography (silica gel, dichloromethane/ethanol 99:1 to 90:10) and obtained as a colorless powder after evaporation to dryness, m.p. 114° C.

Workup

  1. temperaturewarmed for 2 h at 40° C
  2. customThe solvent was removed in vacuo
  3. stirringthe residue stirred with water
  4. filtrationfiltrated by suction
  5. washwashed with water
  6. customThe title compound was purified by column chromatography (silica gel, dichloromethane/ethanol 99:1 to 90:10)
  7. customobtained as a colorless powder
  8. customafter evaporation to dryness, m.p. 114° C.

Sources & evidence

ORD record
ord-b8156c0ff88f43c9b1446157ec6c3ae2
Source dataset
uspto-grants-1996_11
Patent number
US05571813

Reaction notes

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