1,1-Dimethoxyethyl(dimethyl)amine → HCID 58877874, compound

HRID 1664191Notes

Reaction equation

HRID 1664191 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].CO[C:14](OC)([N:16]([CH3:18])[CH3:17])[CH3:15]>CO>[Br:1][C:2]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][C:3]=1[C:4]([N:6]=[C:14]([N:16]([CH3:18])[CH3:17])[CH3:15])=[O:5]

Participants

4

Reactant 2

HCID 878351,1-Dimethoxyethyl(dimethyl)amineHCID 27784642-bromo-5-fluorobenzamide

Product 1

HCID 58877874HCID 58877874, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 2-bromo-5-fluorobenzamide (9.57 g, 43.89 mmol) and N,N-dimethylacetamide dimethyl acetal (20 ml) was heated under argon at 120° C. for 1.5 h. The methanol formed was collected through a reflux condenser. The reaction mixture was allowed to cool and the excess N,N-dimethylacetamide dimethyl acetal was removed under reduced pressure. The residual oil was crystallized from a mixture of ether (30 ml) and hexane (50 ml) to give 9.51 g (75% yield) of the title material as white crystals. 1HNMR 400 MHz (CDCl3) δ (ppm): 2.43 (3H, s, CH3), 3.16 (3H, s, NCH3), 3.19 (3H, s, NCH3), 6.90-6.97 (1H, m, aromatic), 7.46 (1H, dd, J=3.1 Hz and J=9.1 Hz, aromatic), 7.53 (1H, dd, J=5.1 Hz and J=9.1 Hz, aromatic). MS (ESI+) m/e 287 [M+H+].

Workup

  1. customwas collected through a reflux condenser
  2. temperatureto cool
  3. customthe excess N,N-dimethylacetamide dimethyl acetal was removed under reduced pressure
  4. customThe residual oil was crystallized from a mixture of ether (30 ml) and hexane (50 ml)

Sources & evidence

ORD record
ord-fe7013f53c8d4f9bb1697574831c2a6c
Source dataset
uspto-grants-2011_10
Patent number
US08039458B2

Reaction notes

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