Dimethylformamide → HCID 178522035, compound

HRID 35027

Reaction equation

HRID 35027 reaction equation
[F:1][C:2]([F:23])([C:16]([F:22])([F:21])[C:17]([F:20])([F:19])[F:18])[C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][C:14]#[N:15])=[CH:8][CH:7]=1)=[O:4].[N-:24]=[N+:25]=[N-:26].[Na+].[Cl-].[NH4+].CN(C)C=O>O>[F:1][C:2]([F:23])([C:16]([F:21])([F:22])[C:17]([F:19])([F:20])[F:18])[C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][C:14]2[NH:26][N:25]=[N:24][N:15]=2)=[CH:8][CH:7]=1)=[O:4]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 212977082,2,3,3,4,4,4-heptafluoro-N-[4-(2-cyanoethyl)phenyl]butanamide

Product 1

HCID 178522035HCID 178522035, compoundYield 43.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
130 °C

Procedure

A mixture of 2,2,3,3,4,4,4-heptafluoro-N-[4-(2-cyanoethyl)phenyl]butanamide (3.9 g), sodium azide (3.7 g), ammonium chloride (3 g) and dimethylformamide (60 mL) was stirred under a nitrogen atmosphere and heated in a 130° C. oil bath for 48 hours. Water (300 mL) was added to the hot mixture to dissolve all suspended salts and the solution was allowed to cool to room temperature. More water was added and the precipitate was collected by filtration. The tan solid was dried at 65° C. in vacuo overnight and recrystallized from a hexane/tetrahydrofuran mixture to give 1.9 g (43% yield) of the title compound as a tan solid, m.p. 161°-162° C.

Workup

  1. dissolutionto dissolve all suspended salts
  2. temperatureto cool to room temperature
  3. filtrationthe precipitate was collected by filtration
  4. customThe tan solid was dried at 65° C. in vacuo overnight
  5. customrecrystallized from a hexane/tetrahydrofuran mixture

Sources & evidence

ORD record
ord-9153dc27639e4a4bb14481582c20460a
Source dataset
uspto-grants-1988_08
Patent number
US04764623

Linked notes

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