Methylamine → HCID 20121408, compound

HRID 572561Notes

Reaction equation

HRID 572561 reaction equation
[C:1]([C:3]1[CH:10]=[CH:9][C:6]([CH2:7]Br)=[C:5]([F:11])[CH:4]=1)#[N:2].[CH3:12][NH2:13]>C1COCC1>[F:11][C:5]1[CH:4]=[C:3]([CH:10]=[CH:9][C:6]=1[CH2:7][NH:13][CH3:12])[C:1]#[N:2]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 27831494-(Bromomethyl)-3-fluorobenzonitrile

Product 1

HCID 20121408HCID 20121408, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-cyano-2-fluoro-benzylbromide (FluoroChem ltd, 16 g, 74 mmol) in dry THF (50 mL) was added to a 40% aqueous solution of methyl amine (700 mL) at 5-10° C. and allowed to stir for 5 min. The reaction mixture was extracted with DCM and the solvent was dried over Na2SO4 and concentrated under vacuum, affording (12.0 g, 95%) of the title compound as a brown liquid. 1H NMR (DMSO-d6, 400 MHz) δ 7.79-7.75 (m, 1H), 7.68-7.61 (m, 2H), 3.71 (s, 2H), 2.24 (s, 3H).

Workup

  1. extractionThe reaction mixture was extracted with DCM
  2. dry with materialthe solvent was dried over Na2SO4
  3. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-71570d2a2d704c779163cb96166d8423
Source dataset
uspto-grants-2015_05
Patent number
US09029405B2

Reaction notes

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