Hydrochloric Acid → HCID 18318150, compound

HRID 1700294Notes

Reaction equation

HRID 1700294 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:5]#[N:6].C(=O)([O-])[O-].[K+].[K+].[Cl:24][CH2:25][C:26](Cl)=[O:27].Cl>CC(C)=O>[Cl:24][CH2:25][C:26]([NH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:5]#[N:6])=[O:27]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6577Chloroacetyl chlorideHCID 11430Potassium CarbonateHCID 183181273-Amino-4-(benzyloxy)benzonitrilato

Product 1

HCID 18318150HCID 18318150, compoundYield 88.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A slurry of 3-amino-4-(benzyloxy)benzonitrile (7 g, 31.2 mmol) and anhydrous potassium carbonate (8.6 g, 62.4 mmol) in 50 mL of acetone was stirred under nitrogen as chloroacetylchloride (2.6 mL, 33 mmol) was added portion-wise. The reaction was stirred overnight. The reaction was poured into ice water and the liquid was neutralized with 6 N hydrochloric acid. The resulting solid was isolated by filtration, washed with water, and dried under reduced pressure to give 3-((chloromethyl)carbonylamino)-4-(benzyloxy)benzonitrile (8.3 g) as a white solid; NMR (CDCl3, TMS) δ4.22 (s, 2), 5.23 (s, 2), 7.03 (d, 1), 7.43 (m, 7), 8.73 (d, 1).

Workup

  1. additionwas added portion-wise
  2. customThe resulting solid was isolated by filtration
  3. washwashed with water
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-0129dc76092c44c08c95947cebc0dc4c
Source dataset
uspto-grants-2002_02
Patent number
US06350761B1

Reaction notes

Loading…