Water → HCID 178522028, compound

HRID 35017Notes

Reaction equation

HRID 35017 reaction equation
[F:1][C:2]([F:22])([C:15]([F:21])([F:20])[C:16]([F:19])([F:18])[F:17])[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-:23]=[N+:24]=[N-:25].[Na+].[Cl-].[NH4+].O>CN(C)C=O>[F:1][C:2]([F:22])([C:15]([F:20])([F:21])[C:16]([F:19])([F:18])[F:17])[C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C:13]2[NH:25][N:24]=[N:23][N:14]=2)=[CH:8][CH:7]=1)=[O:4]

Participants

6

Reactant 4

HCID 962Water2×HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 142538042,2,3,3,4,4,4-heptafluoro-N-[4-(cyanomethyl)phenyl]butanamide

Product 1

HCID 178522028HCID 178522028, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2,2,3,3,4,4,4-heptafluoro-N-[4-(cyanomethyl)phenyl]butanamide (17.5 g.), sodium azide (17.3 g.) and ammonium chloride (14.1 g.) was heated in dimethylformamide (250 ml.) at 130°-135° C. (oil bath) under a nitrogen atmosphere for 20 hours. Enough water was then added to the hot reaction mixture to dissolve all suspended salts and the mixture was allowed to cool to room temperature. Additional water was then added to produce a white precipitate which was filtered, washed with water and dried under vacuum. The white solid 2,2,3,3,4,4,4-heptafluoro-N-[4-(1H-tetrazol-5-ylmethyl)phenyl]butanamide product (8.7 g., 44%, mp 176°-179° C.) was analytically pure as isolated. A sample recrystallized from acetone (minimum amount)/diethyl ether melted at 176°-178° C.

Workup

  1. dissolutionto dissolve all suspended salts
  2. customto produce a white precipitate which
  3. filtrationwas filtered
  4. washwashed with water
  5. customdried under vacuum
  6. customas isolated
  7. customA sample recrystallized from acetone (minimum amount)/diethyl ether melted at 176°-178° C.

Sources & evidence

ORD record
ord-8044a0fbde384ffdb912aea6da3ed79b
Source dataset
uspto-grants-1988_08
Patent number
US04764623

Reaction notes

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