Ammonia → 3-Fluoro-4-(5-pentyl-1,3-dioxan-2-yl)-benzonitrile

HRID 246875Notes

Reaction equation

HRID 246875 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH:11]1[O:16][CH2:15][CH:14]([CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH2:13][O:12]1)[C:5](O)=O.O=S(Cl)Cl.[NH3:26]>>[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH:11]1[O:16][CH2:15][CH:14]([CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH2:13][O:12]1)[C:5]#[N:26]

Participants

4

Reactant 3

HCID 222AmmoniaHCID 24386Thionyl ChlorideHCID 201624993-Fluoro-4-(5-pentyl-1,3-dioxan-2-yl)-benzoic acid

Product 1

HCID 201621573-Fluoro-4-(5-pentyl-1,3-dioxan-2-yl)-benzonitrile

Conditions

Temperature
20 °C

Procedure

As described in Example 9 4.44 gms. of 3-fluoro-4-(5-pentyl-1,3-dioxan-2-yl)-benzoic acid are converted by SOCl2 into the acid chloride. After removing excess SOCl2 the residue obtained is added to aqueous ammonia and stirred for 4 hours at 20° C. The precipitated acid amide is filtrated by suction and dried. For conversion into the nitrile it is dissolved in 50 ml of pyridine and 10 ml of POCl3, then stirred at 20° C. for 20 hours and evaporated. Thus 3-fluoro-4-(5-pentyl-1,3-dioxan-2-yl)-benzonitrile is obtained.

Workup

  1. customAfter removing excess SOCl2 the residue
  2. customobtained
  3. filtrationThe precipitated acid amide is filtrated by suction
  4. customdried
  5. dissolutionFor conversion into the nitrile it is dissolved in 50 ml of pyridine
  6. stirring10 ml of POCl3, then stirred at 20° C. for 20 hours
  7. customevaporated

Sources & evidence

ORD record
ord-b642ce8d36d54bfcaaa5052a39948671
Source dataset
uspto-grants-1987_11
Patent number
US04704227

Reaction notes

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