Methylamine → 3-(3,4-Dichlorophenoxy)-N-methylazetidine-1-carboxamide

HRID 1032136Notes

Reaction equation

HRID 1032136 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][C:15]=1[Cl:16])[O:5][CH:6]1[CH2:9][N:8]([C:10](Cl)=[O:11])[CH2:7]1.[CH3:17][NH2:18]>O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][C:15]=1[Cl:16])[O:5][CH:6]1[CH2:9][N:8]([C:10]([NH:18][CH3:17])=[O:11])[CH2:7]1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 15042235HCID 15042235, compound

Product 1

HCID 150422213-(3,4-Dichlorophenoxy)-N-methylazetidine-1-carboxamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 5.6 g (0.02 mole) of 3-(3,4-dichlorophenoxy)-1-azetidinecarbonyl chloride in 20 ml of tetrahydrofuran was stirred while 5 ml (0.06 mole) of 40% aqueous methylamine was added slowly, stirring was continued for 18 hr. The reaction mixture was diluted with 200 ml of ice water, and the solid which formed was collected by filtration, 6.9 g. The crude wet solid was recrystallized from ethanol/water to yield 3.65 g (66.3%) of greenish-gray plate-like crystals, m.p. 158°-159° C.

Workup

  1. additionwas added slowly
  2. customthe solid which formed
  3. filtrationwas collected by filtration, 6.9 g
  4. customThe crude wet solid was recrystallized from ethanol/water
  5. customto yield 3.65 g (66.3%) of greenish-gray plate-like crystals, m.p. 158°-159° C.

Sources & evidence

ORD record
ord-7abc65d90ba44999b3f9f914b5bb1afd
Source dataset
uspto-grants-1990_09
Patent number
US04956359

Reaction notes

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