Chloride → HCID 68754990, compound

HRID 2039972Notes

Reaction equation

HRID 2039972 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:9]([CH3:12])=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].C(N([CH2:18][CH3:19])CC)C.[Cl-:20]>ClCCl>[CH3:8][O:7][C:5](=[O:6])[C:4]1[CH:3]=[C:2]([NH:1][C:5](=[O:6])[C:4]2[CH:9]=[CH:10][C:19]([CH2:18][Cl:20])=[CH:2][CH:3]=2)[CH:11]=[CH:10][C:9]=1[CH3:12]

Participants

5

Reactant 3

HCID 312ChlorideHCID 8471TriethylamineHCID 15049977Methyl 5-Amino-2-methylbenzoate

Product 1

HCID 68754990HCID 68754990, compoundYield 124.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A reactor is charged with 1 g (6.06 mmol) of methyl 3-amino-6-methylbenzoate and 1.2 g (11.9 mmol) of triethylamine in 25 ml of dichloromethane. 1.145 g (6.05 mmol) of 4-chloromethylbenzoyle chloride is then added and the mixture is stirred at room temperature for 2 hours. The reacting medium is then washed with 10 ml of a saturated NaHCO3 solution, 10 ml of water and 10 ml of a saturated NaCl solution. The organic phase is dried, evaporated and the obtained residue is triturated in ethylic ether and then in pentane to give a white solid (1.2 g, 66%).

Workup

  1. washThe reacting medium is then washed with 10 ml of a saturated NaHCO3 solution, 10 ml of water and 10 ml of a saturated NaCl solution
  2. customThe organic phase is dried
  3. customevaporated
  4. customthe obtained residue is triturated in ethylic ether

Sources & evidence

ORD record
ord-3374851e1283438ca4a542dc775a5edc
Source dataset
uspto-grants-2013_11
Patent number
US08580815B2

Reaction notes

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