Diisopropylethylamine → HCID 12789634, compound

HRID 65835Notes

Reaction equation

HRID 65835 reaction equation
Cl[O:2][N:3]=[CH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[CH:11]([C:13]1[CH:22]=[CH:21][CH:20]=[CH:19][C:14]=1[C:15]([O:17][CH3:18])=[O:16])=[CH2:12].C(N(C(C)C)C(C)C)C>CCOCC>[C:5]1([C:4]2[CH2:12][CH:11]([C:13]3[CH:22]=[CH:21][CH:20]=[CH:19][C:14]=3[C:15]([O:17][CH3:18])=[O:16])[O:2][N:3]=2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 12541466Methyl 2-ethenylbenzoateHCID 53951592Benzaldehyde chlorooxime

Product 1

HCID 12789634HCID 12789634, compoundYield 79.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

To a stirred solution of 9.4 g (0.0604 mol) of benzaldehyde chlorooxime and 10.76 g (0.0664 mol) of methyl o-vinyl-benzoate in 100 ml of ether at 0°-5° C. was added dropwise a solution of 7.81 g (0.0604 mol) of ethyldiisopropylamine in 35 ml of ether during 30 minutes. The mixture was stirred in an ice bath for 4 hours, diluted with another 400 ml of ether, extracted three times with water, and concentrated under vacuum to a solid. This solid was washed with 200 ml of hexane. The undissolved solid product, 14.21 g, had mp 90°-94° C. Crystallization of this from 100 ml of methanol gave 13.50 g (79%) of white solid, mp 93.5°-95° C.

Workup

  1. extractionextracted three times with water
  2. concentrationconcentrated under vacuum to a solid
  3. washThis solid was washed with 200 ml of hexane
  4. customCrystallization of this from 100 ml of methanol

Sources & evidence

ORD record
ord-825c82a8ba72437cbb0615faf38edadf
Source dataset
uspto-grants-1978_12
Patent number
US04129568

Reaction notes

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