Chloroacetonitrile → HCID 22748760, compound

HRID 1390327Notes

Reaction equation

HRID 1390327 reaction equation
[C:1]1([CH:7]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:8]2[CH:9]=[CH:10][C:11]([C:14]([OH:16])=[O:15])=[N:12][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:23]([N:25](CC)CC)[CH3:24].ClCC#N>CC(C)=O>[C:17]1([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:8]2[CH:9]=[CH:10][C:11]([C:14]([O:16][CH2:24][C:23]#[N:25])=[O:15])=[N:12][CH:13]=2)[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 7856ChloroacetonitrileHCID 8471TriethylamineHCID 22748764HCID 22748764, compound

Product 1

HCID 22748760HCID 22748760, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
25 °C

Procedure

Suspend 4.3 g. (0.015 mole) of 5-(diphenylmethyl)-picolinic acid in 100 ml. of acetone with stirring and add 2.3 g. (0.023 mole) of triethylamine. To the resulting solution add dropwise 1.7 g. (0.023 mole) of chloroacetonitrile. Stir the reaction mixture at room temperature (25° C.) for 15 minutes, then reflux for 4 hours. Cool and filter the reaction mixture. Concentrate the filtrate to a residue in vacuo and triturate the residue with hot isopropyl ether to yield the product of this example, yield 3.5 g., m.p. 95°-98° C.

Workup

  1. additionadd 2.3 g
  2. additionTo the resulting solution add dropwise 1.7 g
  3. temperaturereflux for 4 hours
  4. temperatureCool
  5. filtrationfilter the reaction mixture
  6. concentrationConcentrate the filtrate to a residue in vacuo
  7. customtriturate the residue with hot isopropyl ether
  8. customto yield the product of this example, yield 3.5 g

Sources & evidence

ORD record
ord-d82ba281997a4e9dbc9a82359a13b968
Source dataset
uspto-grants-1979_02
Patent number
US04138488

Reaction notes

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