Water → HCID 15053449, compound

HRID 2081456Notes

Reaction equation

HRID 2081456 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][CH:15]=1)[O:5][CH:6]1[CH2:9][N:8]([C:10](Cl)=[O:11])[CH2:7]1.C(=O)([O-])[O-].[K+].[K+].[CH2:22]([NH2:25])[C:23]#[CH:24].O>O1CCCC1>[Br:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][CH:15]=1)[O:5][CH:6]1[CH2:9][N:8]([C:10]([NH:25][CH2:22][C:23]#[CH:24])=[O:11])[CH2:7]1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 239041PropargylamineHCID 15053365HCID 15053365, compound

Product 1

HCID 15053449HCID 15053449, compoundYield 64.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A stirred mixture of 5.8 g (0.02 mole) of 3-(3-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. A piece of ice was added and stirring was continued for 42 hr. The solid residue which remained was stirred with 100 ml of water then filtered, yielding 5.3 g of crude product. Recrystallization from ethanol yielded 4.0 g of fine beige crystals, m.p. 145°-147° C. After drying at 100° C. in vacuo, m.p. was 146°-147° C. (64.7%).

Workup

  1. additionadded dropwise from a needle and syringe
  2. additionA piece of ice was added
  3. filtrationthen filtered
  4. customyielding 5.3 g of crude product
  5. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-17bc16377d014411b858bd9acf9c4cf7
Source dataset
uspto-grants-1993_02
Patent number
US05183902

Reaction notes

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