Diethyl Ether → HCID 21516386, compound

HRID 1283801Notes

Reaction equation

HRID 1283801 reaction equation
[Na].[C:2]([C:4]1[CH:9]=[CH:8][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:6][C:5]=1[N:14]=[N:15][NH:16][C:17]1[CH:22]=[C:21]([C:23]([F:26])([F:25])[F:24])[CH:20]=[CH:19][C:18]=1[C:27]#[N:28])#[N:3].[H-].[Na+].[C:31](Cl)(=[O:37])[CH2:32][CH2:33][C:34](Cl)=[O:35].CC[O:41]CC>>[C:31]([CH2:32][CH2:33][C:34]([N:14]([C:5]1[CH:6]=[C:7]([C:10]([F:13])([F:12])[F:11])[CH:8]=[CH:9][C:4]=1[C:2]#[N:3])[N:15]=[N:16][C:17]1[CH:22]=[C:21]([C:23]([F:24])([F:25])[F:26])[CH:20]=[CH:19][C:18]=1[C:27]#[N:28])=[O:35])([OH:37])=[O:41]

Participants

6

Reactant 5

HCID 3283Diethyl Ether2×HCID 10970Succinyl chlorideHCID 24758Sodium hydrideHCID 30354951,3-Bis(2-cyano-5-(trifluoromethyl)phenyl)triazeneHCID 5360545Sodium

Product 1

HCID 21516386HCID 21516386, compound

Procedure

A solution of the sodium salt prepared from 10.0 g. (0.026 mol.) of 1,3-bis(2-cyano-5-trifluoromethylphenyl)-triazene and 1.4 g. (0.029 mol.) of sodium hydride in 700 ml. of ether is added dropwise to a solution of 4.65 g. (0.03 mol.) of succinyl chloride in 150 ml. of ether. The reaction mixture is stirred for 12 hours at 25°, filtered and the filtrate is concentrated in vacuo. The residue is washed with hexane, ether is added and the precipitate is removed by filtration. The volume is brought to 500 ml. with ether and a small amount of water is added. The mixture is stirred for 12 hours and the ethereal solution is dried (MgSO4) and concentrated in vacuo to give 3-(3-carboxypropionyl)-1,3-bis(2-cyano-5-trifluoromethylphenyl)triazene.

Workup

  1. filtrationfiltered
  2. concentrationthe filtrate is concentrated in vacuo
  3. washThe residue is washed with hexane, ether
  4. additionis added
  5. customthe precipitate is removed by filtration
  6. additionwith ether and a small amount of water is added
  7. stirringThe mixture is stirred for 12 hours
  8. dry with materialthe ethereal solution is dried (MgSO4)
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7ba1123592ce4a648f6e79b7cf0a1bff
Source dataset
uspto-grants-1976_08
Patent number
US03976633

Reaction notes

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