Ethanol → HCID 54029986, compound

HRID 2380725Notes

Reaction equation

HRID 2380725 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][C:7]#[N:8])=[CH:4][CH:3]=1.[OH-].[Na+].[CH3:13][CH2:14]O>C(Cl)(Cl)(Cl)Cl.[Cl-].C[N+](C)(C)CC1C=CC=CC=1>[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](=[C:6]([C:13]2[CH:14]=[CH:10][C:2]([F:1])=[CH:3][CH:4]=2)[C:7]#[N:8])[C:7]#[N:8])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 68016Benzeneacetonitrile, 4-fluoro-

Product 1

HCID 54029986HCID 54029986, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 5963Benzyltrimethylammonium chlorideCatalystHCID 5943Carbon TetrachlorideSolvent2×

Procedure

A solution of 4-fluorobenzyl cyanide (30 g; ##STR21## 0.222 mol.) in carbon tetrachloride (100 ml) was added slowly, over a period of 30 minutes, to a rapidly stirring mixture of 40% aqueous sodium hydroxide (100 ml; 1 mol), carbon tetrachloride (100 ml) and trimethylbenzylammonium chloride (TMBA; 0.6 g; 0.003 mol). The mixture was maintained at room temperature overnight, after which time a precipitate had formed which was collected by filtration and washed with water and chloroform. The organic layer of the mother liquor was washed successively with dilute hydrochloric acid, 5% aqueous sodium bicarbonate and water and then dried over magnesium sulphate. The dried solution was filtered and then evaporated to a paste which was triturated with ethanol to give a second crop of product, which was combined with the first. The material was recrystalised form ethanol to yield small white needles. Yield=50%.: m.p. 194°-195° (EtOH); 1H NMR (200 MHz, CDCl3) d 7.17-7.29 (m, 4H), 7.78-7.89 (m, 4H); 13C NMR (50 MHz, DMSO-d6) d 116.74 (d, |J|=22.4 Hz), 116.76 (s), 124.81 (s), 128.59 (d, |J|=3.4 Hz), 131.73 (d, |J|=1 Hz), 163.87 (d, |J|=250.6 Hz); MS (El) m/e 266 (100, M+.); Analysis calc'd for C16H8N2F2: C, 72.17; H, 3.03; N, 10.52; found: C, 71.98; H, 2.80; N, 10.48.

Workup

  1. customafter which time a precipitate had formed which
  2. filtrationwas collected by filtration
  3. washwashed with water and chloroform
  4. washThe organic layer of the mother liquor was washed successively with dilute hydrochloric acid, 5% aqueous sodium bicarbonate and water
  5. dry with materialdried over magnesium sulphate
  6. filtrationThe dried solution was filtered
  7. customevaporated to a paste which
  8. customwas triturated with ethanol
  9. customto give a second crop of product, which
  10. customThe material was recrystalised form ethanol
  11. customto yield small white needles

Sources & evidence

ORD record
ord-a4bbd87e6ebf42a99e4a9b6e44bc6834
Source dataset
uspto-grants-1994_11
Patent number
US05369203

Reaction notes

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