1,1-bis(1,1-dimethylethoxy)-N,N,N-trimethylamine → 5-Bromo-2-(dimethylamino-methyleneamino)-3-methyl-benzoic acid tert-butyl ester

HRID 583362Notes

Reaction equation

HRID 583362 reaction equation
[NH2:1][C:2]1[C:10]([CH3:11])=[CH:9][C:8]([Br:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].C(O[CH:18](OC(C)(C)C)[N:19]([CH3:21])[CH3:20])(C)(C)C>C1(C)C=CC=CC=1>[C:3]([O:5][C:4](=[O:6])[C:3]1[CH:7]=[C:8]([Br:12])[CH:9]=[C:10]([CH3:11])[C:2]=1[N:1]=[CH:18][N:19]([CH3:21])[CH3:20])([CH3:7])([CH3:4])[CH3:2]

Participants

4

Reactant 2

HCID 5477121,1-bis(1,1-dimethylethoxy)-N,N,N-trimethylamineHCID 118503832-Amino-5-bromo-3-methylbenzoic acid

Product 1

HCID 540146925-Bromo-2-(dimethylamino-methyleneamino)-3-methyl-benzoic acid tert-butyl esterYield 97.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 5.0 g (21.7 mmol) of the product of Example 132 and 20.8 ml (86.9 mmol) of N,N-dimethylformamide di-t-butylacetal in 30 ml of toluene was heated to reflux for 2 hr. The reaction mixture was cooled to room tenperature, washed with water and brine, dried over MgSO4 and concentrated in vacuo to provide 3.61 g (49%) of the desired product as an yellow oil. Electrospray Mass Spec 341(M+H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 2 hr
  3. temperatureThe reaction mixture was cooled to room tenperature
  4. washwashed with water and brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fb49ab09e1cc4f558dd63dc41eccd7fe
Source dataset
uspto-grants-1999_07
Patent number
US05929097

Reaction notes

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