Benzoyl chloride → 3-cyano-N-[4-(benzoylamino)-benzyl]-benzamide

HRID 31499Notes

Reaction equation

HRID 31499 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:10]([C:12]1[CH:13]=[C:14]([CH:26]=[CH:27][CH:28]=1)[C:15]([NH:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([NH2:25])=[CH:21][CH:20]=1)=[O:16])#[N:11].C(N(CC)CC)C>C(Cl)Cl>[C:10]([C:12]1[CH:13]=[C:14]([CH:26]=[CH:27][CH:28]=1)[C:15]([NH:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([NH:25][C:1](=[O:8])[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:21][CH:20]=1)=[O:16])#[N:11]

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 608931683-cyano-N-(4-amino-benzyl)-benzamide

Product 1

HCID 693086213-cyano-N-[4-(benzoylamino)-benzyl]-benzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 0.6 g (4.2 mmol) of benzoylchloride in 10 ml of methylene chloride is added dropwise to a solution of 1 g (4 mmol) of 3-cyano-N-(4-amino-benzyl)-benzamide and 0.6 g (6 mmol) of triethylamine in 30 ml of methylene chloride at ambient temperature. After 8 hours at ambient temperature the product which has crystallised out is dissolved in methylene chloride and methanol. After extraction with water the combined organic extracts are dried and evaporated down.

Workup

  1. customAfter 8 hours at ambient temperature the product which has crystallised out
  2. dissolutionis dissolved in methylene chloride
  3. extractionAfter extraction with water the combined organic extracts
  4. customare dried
  5. customevaporated down

Sources & evidence

ORD record
ord-2bed51339cdf4881b929757cb7991d35
Source dataset
uspto-grants-2008_09
Patent number
US07425641B2

Reaction notes

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