Methylamine → 1-(1,3-Benzoxazol-2-yl)-N-methylmethanamine

HRID 1091077Notes

Reaction equation

HRID 1091077 reaction equation
Cl[CH2:2][C:3]1[O:4][C:5]2[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=2[N:7]=1.[CH3:12][NH2:13]>O>[CH3:12][NH:13][CH2:2][C:3]1[O:4][C:5]2[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=2[N:7]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 20619892-(Chloromethyl)-1,3-benzoxazole

Product 1

HCID 156759021-(1,3-Benzoxazol-2-yl)-N-methylmethanamineYield 82%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-(Chloromethyl)benzoxazole (3.99 g, 23.8 mmol) was dissolved in aqueous methylamine (40 mL, 40 wt % in H2O) at 10° C. under a nitrogen atmosphere. After 20 minutes, the reaction mixture was warmed to room temperature and stirred for 1 hour. The mixture was diluted with water and extracted with dichloromethane. The organic phase was dried (MgSO4) and concentrated to afford crude product which was purified by flash column chromatography (5% methanol/dichloromethane) to afford 3.18 g (82%) of pure product as a yellow oil.

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialThe organic phase was dried (MgSO4)
  3. concentrationconcentrated
  4. customto afford crude product which
  5. customwas purified by flash column chromatography (5% methanol/dichloromethane)

Sources & evidence

ORD record
ord-51473277bb6b4144b6316a394aff939a
Source dataset
uspto-grants-1992_01
Patent number
US05084463

Reaction notes

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