Chloroacetonitrile → HCID 21333313, compound

HRID 442128Notes

Reaction equation

HRID 442128 reaction equation
[C:1]1([C:7]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)([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.[CH2:29]([N:31](CC)CC)[CH3:30].ClCC#N>CC(C)=O>[C:23]1([C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:8]2[CH:9]=[CH:10][C:11]([C:14]([O:16][CH2:30][C:29]#[N:31])=[O:15])=[N:12][CH:13]=2)[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

5

Reactant 3

HCID 7856ChloroacetonitrileHCID 8471TriethylamineHCID 47264picotrin

Product 1

HCID 21333313HCID 21333313, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a stirred mixture of 5 g. 5-(triphenylmethyl)-picolinic acid and 6.1 g. triethylamine in 150 ml. acetone add 4.5 g. of chloroacetonitrile. Heat the resulting mixture at reflux 15 hr., cool, filter. Concentrate the filtrate to a residue and triturate residue with water, dry. Recrystallize twice from isopropyl ether-ethanol to obtain the product of this example, m.p. 173°-175°.

Workup

  1. additionTo a stirred mixture of 5 g
  2. temperatureHeat the resulting mixture
  3. temperatureat reflux 15 hr
  4. temperature, cool
  5. filtrationfilter
  6. concentrationConcentrate the filtrate to a residue
  7. customtriturate residue with water
  8. customdry
  9. customRecrystallize twice from isopropyl ether-ethanol
  10. customto obtain the product of this example, m.p. 173°-175°

Sources & evidence

ORD record
ord-773b8dc5d45843a99b3a6e9b2140ecc0
Source dataset
uspto-grants-1977_08
Patent number
US04044140

Reaction notes

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