Hydrochloric Acid → HCID 19816020, compound

HRID 2247893Notes

Reaction equation

HRID 2247893 reaction equation
[C:1]([C:9]1[CH:10]=[CH:11][C:12]([N+:18]([O-:20])=[O:19])=[C:13]([CH:17]=1)[C:14]([OH:16])=O)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[C:33]1([CH2:39][NH2:40])[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.Cl>O.ClCCl>[C:1]([C:9]1[CH:10]=[CH:11][C:12]([N+:18]([O-:20])=[O:19])=[C:13]([CH:17]=1)[C:14]([NH:40][CH2:39][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:16])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7504BenzylamineHCID 682631,1'-CarbonyldiimidazoleHCID 19816011HCID 19816011, compound

Product 1

HCID 19816020HCID 19816020, compoundYield 72.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To solution of 8.5 parts of intermediate 18, namely 5-benzoyl-2-nitrobenzoic acid, in 66.5 parts of dichloromethane were added 5.3 parts of 1,1'-carbonylbis[1H-imidazole]. After stirring for 1 hour at room temperature, there were added 9.8 parts of benzenemethanamine. Stirring at room temperature was continued for 8 hours. The reaction mixture was diluted with 100 parts of water and acidified with HCl. The organic layer was separated, dried, filtered and evaporated. The residue was purified twice by column chromatography (silica gel; CHCl3 /CH3OH 98:2; CH3COOC2H5 /C6H5CH3 10:90). The eluent of the desired fractions was evaporated and the residue was crystallized from methylbenzene, yielding 8.1 parts (72.5%) of 5-benzoyl-2-nitro-N-(phenylmethyl)benzamide; mp. 167.4° C. (interm. 19).

Workup

  1. stirringStirring at room temperature
  2. waitwas continued for 8 hours
  3. customThe organic layer was separated
  4. customdried
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified twice by column chromatography (silica gel; CHCl3 /CH3OH 98:2; CH3COOC2H5 /C6H5CH3 10:90)
  8. customThe eluent of the desired fractions was evaporated
  9. customthe residue was crystallized from methylbenzene

Sources & evidence

ORD record
ord-f2dbef7d83d141e4852ad52ca6297a69
Source dataset
uspto-grants-1991_08
Patent number
US05037829

Reaction notes

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