Chloride → HCID 11086987, compound

HRID 345752Notes

Reaction equation

HRID 345752 reaction equation
[N+:1]([C:4]1[CH:19]=[CH:18][C:7]([CH2:8][NH:9][C:10](=O)[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[Cl-:20]>S(Cl)(Cl)=O>[N+:1]([C:4]1[CH:19]=[CH:18][C:7]([CH2:8][N:9]=[C:10]([Cl:20])[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 312ChlorideHCID 282107n-(4-nitrobenzyl)benzamide

Product 1

HCID 11086987HCID 11086987, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent

Procedure

A solution of 3.7 mmol of N-(p-nitrobenzyl)-benzamide in thionyl chloride was refluxed under an inert atmosphere for 30 minutes and after cooling, the excess thionyl chloride was removed under vacuum to leave a solid residue. The residue was crystallized from dry cyclohexane under dry nitrogen (Note: the subsequent filtration had to be done under dry nitrogen also to obtain an 85% yield of the purified imidoyl--chloride melting at 71° to 73° C. (Lit. m.pt. 73--4 Huisgen et al--Loc. cit) which was used directly in the next step.

Workup

  1. temperatureafter cooling
  2. customthe excess thionyl chloride was removed under vacuum
  3. customto leave a solid residue
  4. customThe residue was crystallized from dry cyclohexane under dry nitrogen (Note
  5. filtrationthe subsequent filtration
  6. customto obtain an 85% yield of the purified imidoyl

Sources & evidence

ORD record
ord-09e432bad7e34f9a93b89b58e18035dc
Source dataset
uspto-grants-1991_10
Patent number
US05059596

Reaction notes

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