Potassium Carbonate → HCID 15053453, compound

HRID 2081460Notes

Reaction equation

HRID 2081460 reaction equation
[Br:1][C:2]1[CH:15]=[CH:14][C:5]([O:6][CH:7]2[CH2:10][N:9]([C:11](Cl)=[O:12])[CH2:8]2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:22]([NH2:25])[C:23]#[CH:24]>O1CCCC1.O>[Br:1][C:2]1[CH:15]=[CH:14][C:5]([O:6][CH:7]2[CH2:10][N:9]([C:11]([NH:25][CH2:22][C:23]#[CH:24])=[O:12])[CH2:8]2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 239041PropargylamineHCID 15053366HCID 15053366, compound

Product 1

HCID 15053453HCID 15053453, compoundYield 67.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A stirred mixture of 5.8 g (0.02 mole) of 3-(4-bromophenoxy)-1-azetidinecarbonyl chloride and 2.8 g (0.02 mole) of potassium carbonate in 20 ml of tetrahydrofuran was treated with 1.1 g (0.02 mole) of 2-propynylamine added dropwise from a needle and syringe. After stirring for 30 min, approximately 1 g of ice was added and stirring continued for 18 hr. The reaction mixture was diluted with 200 ml of water and the solid which separated was collected by filtration, 6.1 g. After drying, recrystallization from benzene-ligroin yielded 4.2 g (67.9%) of fine white crystals, m.p. 120°-122° C.

Workup

  1. additionadded dropwise from a needle and syringe
  2. stirringstirring
  3. waitcontinued for 18 hr
  4. customthe solid which separated
  5. filtrationwas collected by filtration, 6.1 g
  6. customAfter drying
  7. customrecrystallization from benzene-ligroin

Sources & evidence

ORD record
ord-3dbb7d66a9474238b2966b27b814f8ff
Source dataset
uspto-grants-1993_02
Patent number
US05183902

Reaction notes

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