Benzyl isocyanate → Rac-2-(3-benzyl-ureido)-n-[(4-chloro-phenyl)-phenyl-methyl]-acetamide

HRID 2425181Notes

Reaction equation

HRID 2425181 reaction equation
Cl.[NH2:2][CH2:3][C:4]([NH:6][CH:7]([C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:5].CCN(C(C)C)C(C)C.[CH2:30]([N:37]=[C:38]=[O:39])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>O1CCOCC1>[CH2:30]([NH:37][C:38](=[O:39])[NH:2][CH2:3][C:4]([NH:6][CH:7]([C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:5])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

5

Reactant 3

HCID 76639Benzyl isocyanateHCID 81531DiisopropylethylamineHCID 672464382-Amino-N-[(4-chloro-phenyl)-phenyl-methyl]-acetamide hydrochloride

Product 1

HCID 59689162Rac-2-(3-benzyl-ureido)-n-[(4-chloro-phenyl)-phenyl-methyl]-acetamideYield 93%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 0.2 mmol rac-2-amino-N-[(4-chloro-phenyl)-phenyl-methyl]-acetamide hydrochloride (Example 3.1) and 0.28 mmol of DIPEA in 2 ml of dioxane was treated with 0.2 mmol of benzylisocyanate. The mixture was stirred at room temperature for 48 hours, concentrated and diluted with diethyl ether. The solid was filtered off, dissolved in dichloromethane and extracted 2 times with a diluted solution of citric acid. The organic phase was dried and concentrated. The residue was triturated with diethyl ether to give the title compound as a colorless solid. Yield=93%.

Workup

  1. concentrationconcentrated
  2. additiondiluted with diethyl ether
  3. filtrationThe solid was filtered off
  4. dissolutiondissolved in dichloromethane
  5. extractionextracted 2 times with a diluted solution of citric acid
  6. customThe organic phase was dried
  7. concentrationconcentrated
  8. customThe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-02f46bf0dde04b60ba2b9ed0774b1d53
Source dataset
uspto-grants-2011_06
Patent number
US07964645B2

Reaction notes

Loading…