Dimethylamine → Methyl 2-(3-((dimethylamino)methyl)phenyl)benzo[d]oxazole-7-carboxylate

HRID 415218Notes

Reaction equation

HRID 415218 reaction equation
Br[CH2:2][C:3]1[CH:4]=[C:5]([C:9]2[O:10][C:11]3[C:17]([C:18]([O:20][CH3:21])=[O:19])=[CH:16][CH:15]=[CH:14][C:12]=3[N:13]=2)[CH:6]=[CH:7][CH:8]=1.[CH3:22][NH:23][CH3:24]>C(O)C>[CH3:22][N:23]([CH2:2][C:3]1[CH:4]=[C:5]([C:9]2[O:10][C:11]3[C:17]([C:18]([O:20][CH3:21])=[O:19])=[CH:16][CH:15]=[CH:14][C:12]=3[N:13]=2)[CH:6]=[CH:7][CH:8]=1)[CH3:24]

Participants

4

Reactant 2

HCID 674DimethylamineHCID 66620978Methyl 2-(3-(bromomethyl)phenyl)benzo[d]oxazole-7-carboxylate

Product 1

HCID 66621354Methyl 2-(3-((dimethylamino)methyl)phenyl)benzo[d]oxazole-7-carboxylateYield 119.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Methyl 2-(3-(bromomethyl)phenyl)benzo[d]oxazole-7-carboxylate (70 mg, 0.2 mmol) and dimethylamine (72 mg, 1.6 mmol) were added to ethanol (30 mL) and the mixture was stirred at room temperature for 1 hr. The resulting mixture was evaporated under reduced pressure to obtain methyl 2-(3-((dimethylamino)methyl)phenyl)benzo[d]oxazole-7-carboxylate (74 mg, yield 86%). LC-MS (ESI) m/z 310 [M+1]+.

Workup

  1. customThe resulting mixture was evaporated under reduced pressure

Sources & evidence

ORD record
ord-8ebd242371194abaadcfb8f77bec2afb
Source dataset
uspto-grants-2012_01
Patent number
US08088760B2

Reaction notes

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