Benzene → HCID 15053443, compound

HRID 2081449Notes

Reaction equation

HRID 2081449 reaction equation
[Cl: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].C1C=CC=CC=1>O1CCCC1.O>[Cl: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

7

Reactant 4

HCID 241BenzeneHCID 11430Potassium CarbonateHCID 239041PropargylamineHCID 15042229HCID 15042229, compound

Product 1

HCID 15053443HCID 15053443, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A stirred mixture of 7.4 g (0.03 mole) of 3-(4-chlorophenoxy)-1-azetidinecarbonyl chloride and 4.5 g (0.03 mole) of potassium carbonate in 20 ml of tetrahydrofuran was treated with 1.7 g (0.03 mole) of 2-propynylamine added dropwise from a needle and syringe. After stirring for 16 hr, the reaction mixture was diluted with 400 ml of water and the resulting tan solid was collected by filtration, yielding 7.7 g of crude product. Repeated triturations of the crude product with hot benzene gave upon combining and cooling 1.2 g (15.2%) of tan powder, m.p. 120°-122° C.

Workup

  1. additionadded dropwise from a needle and syringe
  2. filtrationthe resulting tan solid was collected by filtration
  3. customyielding 7.7 g of crude product

Sources & evidence

ORD record
ord-5c78dedd8de846d9b4b1f089f75ecb2f
Source dataset
uspto-grants-1993_02
Patent number
US05183902

Reaction notes

Loading…