Sodium Chloride → HCID 178439048, compound

HRID 2405002Notes

Reaction equation

HRID 2405002 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH:10]([CH3:12])[CH3:11])[C:5]=1[N:13]=[C:14]([C:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][C:24]=2[C:26]([OH:28])=[O:27])[C:19]([C:29]#[C:30][CH2:31][CH2:32][CH2:33][CH2:34]OS(C2C=CC(C)=CC=2)(=O)=O)=[CH:18][CH:17]=1)[OH:15])([CH3:3])[CH3:2].[N-:46]=[N+:47]=[N-:48].[Na+].[Cl-].[Na+]>C(O)(=O)C>[CH:10]([C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([CH:1]([CH3:3])[CH3:2])[C:5]=1[N:13]=[C:14]([C:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][C:24]=2[C:26]([OH:28])=[O:27])[C:19]([C:29]#[C:30][CH2:31][CH2:32][CH2:33][CH2:34][N:46]=[N+:47]=[N-:48])=[CH:18][CH:17]=1)[OH:15])([CH3:11])[CH3:12]

Participants

5

Reactant 3

HCID 5234Sodium ChlorideHCID 33557Sodium AzideHCID 178427728HCID 178427728, compound

Product 1

HCID 178439048HCID 178439048, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 0.50 g (0.82 mmol) N-(2,6-diisopropylphenyl)-4-(6-tosyloxy-1-hexinyl)-naphthaline-1,8-dicarboxylic acid imide and 0.36 g (5.5 mmol) sodium azide were stirred for 17 hours at room temperature under nitrogen atmosphere. 250 ml acetic acid and saturated sodium chloride solution were added to the reaction mixture. After mixing, the organic phase was removed and washed once with saturated sodium chloride solution and two times with water. The organic phase was dried with MgSO4 and the solvent was evaporated in a rotary evaporator at a temperature of the water-bath of 25° C. The obtained oil (0.40 g) was purified on silica gel ((60 Å, 60-200 μm) free flow agent: methylene chloride. 0.10 g (25% of the theoretical yield) of a orange-yellow solid material were obtained.

Workup

  1. additionAfter mixing
  2. customthe organic phase was removed
  3. washwashed once with saturated sodium chloride solution and two times with water
  4. dry with materialThe organic phase was dried with MgSO4
  5. customthe solvent was evaporated in a rotary evaporator at a temperature of the water-bath of 25° C
  6. customThe obtained oil (0.40 g) was purified on silica gel ((60 Å, 60-200 μm) free flow agent
  7. custom0.10 g (25% of the theoretical yield) of a orange-yellow solid material
  8. customwere obtained

Sources & evidence

ORD record
ord-35af13d112d44ebab115517961478317
Source dataset
uspto-grants-2014_08
Patent number
US08802852B2

Reaction notes

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