Methylamine → HCID 23158201, compound

HRID 1619298Notes

Reaction equation

HRID 1619298 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]([Br:11])[CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].ClC(Cl)(OC(=O)OC(Cl)(Cl)Cl)Cl.[CH3:24][NH2:25]>O1CCOCC1>[NH2:1][C:2]1[CH:10]=[C:9]([Br:11])[CH:8]=[CH:7][C:3]=1[C:4]([NH:25][CH3:24])=[O:5]

Participants

5

Reactant 3

HCID 6329MethylamineHCID 886912-Amino-4-bromobenzoic acidHCID 94429Triphosgene

Product 1

HCID 23158201HCID 23158201, compoundYield 86.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a mixture of 2-amino-4-bromobenzoic acid (5.0 g, 23.1 mmol) and dioxane (50 mL) was added triphosgene (2.3 g, 7.75 mmol). The reaction mixture was heated to reflux and stirred for 4 h. Methylamine (40% in water, 2 mL, 23.1 mmol) was added dropwise after the mixture was cooled to room temperature. After stirring for 30 min, the solution was evaporated under reduced pressure and the residue was redissolved in DCM which was washed with sat. NaHCO3 aqueous solution, dried over Na2SO4, filtered, and evaporated to give 4.6 g of the target compound. MS (ESI): 229, 231 (MH+).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux
  3. stirringAfter stirring for 30 min
  4. customthe solution was evaporated under reduced pressure
  5. dissolutionthe residue was redissolved in DCM which
  6. washwas washed with sat. NaHCO3 aqueous solution
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-9d4f998400e7414797c4d02e98f177b9
Source dataset
uspto-grants-2014_07
Patent number
US08772301B2

Reaction notes

Loading…