Triethylamine → HCID 18541413, compound

HRID 411756Notes

Reaction equation

HRID 411756 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([Cl:11])[CH:3]=1.C(N([CH2:17][CH3:18])CC)C>CN(C=O)C>[Cl:11][C:4]1[CH:3]=[C:2]([NH:1][C:6]([CH2:5][C:4]2[CH:3]=[CH:2][CH:10]=[CH:9][C:17]=2[CH3:18])=[O:7])[CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=[O:7]

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 171544-Amino-2-chlorobenzoic acid

Product 1

HCID 18541413HCID 18541413, compoundYield 107.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

19.56 g (116 mmol) of (2-methylphneyl)acetic acid chloride are added, over 1 hour, to a mixture of 20 g (116 mmol) of 4-amino-2-chlorobenzoic acid, 12.9 g (127 mmol) of triethylamine and 150 ml of DMF dried over a molecular sieve. After stirring for 16 h at room temperature, the DMF is removed by evaporation under vacuum. The residue is washed with water and with dichloromethane to give, after drying, 19 g of an off-white powder (Yield=53%).

Workup

  1. customdried over a molecular sieve
  2. customthe DMF is removed by evaporation under vacuum
  3. washThe residue is washed with water and with dichloromethane
  4. customto give
  5. customafter drying

Sources & evidence

ORD record
ord-7a1e6255d4554b90ab9c4e8107e256d5
Source dataset
uspto-grants-2003_05
Patent number
US06559185B2

Reaction notes

Loading…