Dimethylformamide → HCID 178522027, compound

HRID 35023Notes

Reaction equation

HRID 35023 reaction equation
[F:1][C:2]([F:25])([C:15]([F:24])([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][C:13]#[N:14])=[CH:8][CH:7]=1)=[O:4].[N-:26]=[N+:27]=[N-:28].[Na+].[Cl-].[NH4+].CN(C)C=O>O>[F:1][C:2]([F:25])([C:15]([F:23])([F:24])[C:16]([F:22])([F:21])[C:17]([F:20])([F:18])[F:19])[C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C:13]2[NH:28][N:27]=[N:26][N:14]=2)=[CH:8][CH:7]=1)=[O:4]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 142538082,2,3,3,4,4,5,5,5-nonafluoro-N-[4-(cyanomethyl)phenyl]pentanamide

Product 1

HCID 178522027HCID 178522027, compoundYield 44.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
135 °C

Procedure

A mixture of 2,2,3,3,4,4,5,5,5-nonafluoro-N-[4-(cyanomethyl)phenyl]pentanamide (6.8 g), sodium azide (5.56 g), ammonium chloride (4.53 g) and dimethylformamide (100 mL) were heated in a 135° C. oil bath under a nitrogen atmosphere overnight. Enough water was added to the hot reaction mixture to dissolve all suspended salts, the mixture was cooled to room temperature and more water was added until a precipitate formed. The solid was collected, washed with water and air dried. Recrystallization from ethylacetate/diethyl ether mixture yielded 3.4 g of the title compound as white flakes, m.p. 173°-174° C. The filtrate produced a second crop of 1.1 g of the title compound.

Workup

  1. dissolutionto dissolve all suspended salts
  2. temperaturethe mixture was cooled to room temperature
  3. customformed
  4. customThe solid was collected
  5. washwashed with water and air
  6. customdried
  7. customRecrystallization from ethylacetate/diethyl ether mixture

Sources & evidence

ORD record
ord-6cb10a10ba9d429ca174241b4f61d37a
Source dataset
uspto-grants-1988_08
Patent number
US04764623

Reaction notes

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