Hydrochloric Acid → HCID 19906262, compound

HRID 2371690Notes

Reaction equation

HRID 2371690 reaction equation
[ClH:1].[F:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][C:10]#[N:11].[CH2:12]([OH:14])[CH3:13]>>[ClH:1].[F:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][C:10](=[NH:11])[O:14][CH2:12][CH3:13]

Participants

4

Reactant 3

HCID 313Hydrochloric Acid2×HCID 702EthanolHCID 67592Benzeneacetonitrile, 2-fluoro-

Product 1

HCID 19906262HCID 19906262, compoundYield 91.5%

Procedure

Dry hydrogen chloride gas (29.8 g, 0.817 mol) was bubbled through a solution of 2-fluorophenylacetonitrile (100 g, 0.743 mol) (Aldrich) in absolute ethanol (37.6 g, 0.817 mol) at 0° C. After uptake of hydrogen chloride was complete, the reaction was kept at 0° C. for 48 hours. The solid was triturated in ether (3×200 mL) and the white solid was collected by suction filtration. Drying for several days under vacuum in a desiccator containing sodium hydroxide pellets and phosphorus pentoxide gave 148 g (91%) of ethyl 2-(2-fluorophenyl)acetimidate hydrochloride, mp. 96°-99° C.; nmr (DMSO-d6)L δ11.58 (br s, 2H, NH2), 6.95-7.50 (complex multiplets, 4H, ArH), 4.40 (q, 2H, OCH2), 4.06 (s, 2H, CH2), 1.24 (t, 3H, CH3); ms: m/e 181 (M+), 162 (M-F+), 153 (M-C2H4 +), 136 (M-OEt+), 109 (C7H6F+).

Workup

  1. customThe solid was triturated in ether (3×200 mL)
  2. filtrationthe white solid was collected by suction filtration
  3. customDrying for several days under vacuum in a desiccator
  4. additioncontaining sodium hydroxide pellets and phosphorus pentoxide

Sources & evidence

ORD record
ord-78f1bddf66b14e52b1625a7b153dfb7d
Source dataset
uspto-grants-1992_03
Patent number
US05095018

Reaction notes

Loading…