Ammonia → 2-[3-(2-Nitrophenoxy)phenoxy]propionamide

HRID 1609262Notes

Reaction equation

HRID 1609262 reaction equation
[N+:1]([C:4]1[CH:22]=[CH:21][CH:20]=[CH:19][C:5]=1[O:6][C:7]1[CH:8]=[C:9]([CH:16]=[CH:17][CH:18]=1)[O:10][CH:11]([CH3:15])[C:12](O)=[O:13])([O-:3])=[O:2].C([N:25](CC)CC)C.ClC(OCC)=O.N>C(Cl)Cl>[N+:1]([C:4]1[CH:22]=[CH:21][CH:20]=[CH:19][C:5]=1[O:6][C:7]1[CH:8]=[C:9]([CH:16]=[CH:17][CH:18]=1)[O:10][CH:11]([CH3:15])[C:12]([NH2:25])=[O:13])([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 200844942-[3-(2-Nitrophenoxy)phenoxy]propionic acid

Product 1

HCID 200843872-[3-(2-Nitrophenoxy)phenoxy]propionamideYield 53.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

In 100 ml of methylene chloride were dissolved 6.15 g of 2-[3-(2-nitrophenoxy)phenoxy]propionic acid and 4.2 g of triethylamine, followed by dropwise addition of 2.5 g of ethyl chloroformate at a temperature not exceeding 0° C., and the mixture was further stirred at the same temperature for 30 minutes. The reaction mixture was poured into previously ice-cooled methylene chloride (120 ml) saturated with ammonia gas and the mixture was then stirred at room temperature for 30 minutes. The methylene chloride layer was washed with water (twice), dried and concentrated and the residue was crystallized from methanol and isopropyl ether to give 3.3 g of the title compound.

Workup

  1. customexceeding 0° C.
  2. additionThe reaction mixture was poured into previously ice-
  3. stirringthe mixture was then stirred at room temperature for 30 minutes
  4. washThe methylene chloride layer was washed with water (twice),
  5. customdried
  6. concentrationconcentrated
  7. customthe residue was crystallized from methanol and isopropyl ether

Sources & evidence

ORD record
ord-62a6fc14b4454eabab8b7a3ef86e6f23
Source dataset
uspto-grants-1995_03
Patent number
US05399703

Reaction notes

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