Triethylamine → HCID 18517417, compound

HRID 382857Notes

Reaction equation

HRID 382857 reaction equation
Cl[C:2]([C:4]1[C:5]([Cl:15])=[C:6]([CH:11]=[CH:12][C:13]=1[Cl:14])[C:7]([O:9][CH3:10])=[O:8])=[O:3].Cl.[CH2:17]([O:20][NH2:21])[CH2:18][CH3:19].C(N(CC)CC)C>C(Cl)Cl>[Cl:15][C:5]1[C:4]([C:2]([NH:21][O:20][CH2:17][CH2:18][CH3:19])=[O:3])=[C:13]([Cl:14])[CH:12]=[CH:11][C:6]=1[C:7]([O:9][CH3:10])=[O:8]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12283955O-propylhydroxylamine hydrochlorideHCID 18517406Methyl 3-chlorocarbonyl-2,4-dichlorobenzoate

Product 1

HCID 18517417HCID 18517417, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

10.7 g (0.04 mol) of methyl 3-chlorocarbonyl-2,4-dichlorobenzoate in 100 ml of methylene chloride were slowly added dropwise at 30° C. to a solution of 4.50 g (0.04 mol) of propoxyamine hydrochloride and 4.05 g (0.04 mol) of triethylamine in 200 ml of methylene chloride. After the reaction mixture had been stirred for 2 hours at room temperature, it was washed with dilute phosphoric acid, dried and concentrated. The resulting residue was chromatographed on silica gel (eluent: toluene/ethyl acetate=9/1). This gave 11.50 g of methyl 2,4-dichloro-3-(N-propoxyamino)carbonylbenzoate.

Workup

  1. washit was washed with dilute phosphoric acid
  2. customdried
  3. concentrationconcentrated
  4. customThe resulting residue was chromatographed on silica gel (eluent: toluene/ethyl acetate=9/1)

Sources & evidence

ORD record
ord-f48aac5a4c864de0bdaf58848ace8d5d
Source dataset
uspto-grants-2001_10
Patent number
US06310245B1

Reaction notes

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