Benzene → N-(2,6-dimethyl-4-chlorophenyl)valine

HRID 648269Notes

Reaction equation

HRID 648269 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[NH:9][C@H:10]([C:14]([OH:16])=[O:15])[CH:11]([CH3:13])[CH3:12].[Cl:17]N1C(=O)CCC1=O.C1C=CC=CC=1>CCCCCC>[CH3:8][C:4]1[CH:5]=[C:6]([Cl:17])[CH:7]=[C:2]([CH3:1])[C:3]=1[NH:9][C@H:10]([C:14]([OH:16])=[O:15])[CH:11]([CH3:12])[CH3:13]

Participants

5

Reactant 3

HCID 241Benzene2×HCID 31398Chlorosuccinimide2×HCID 15383894N-(2,6-dimethylphenyl)valine

Product 1

HCID 54357344N-(2,6-dimethyl-4-chlorophenyl)valine

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent2×

Procedure

A mixture of 0.5 g of the m-phenoxybenzyl ester of N-(2,6-dimethylphenyl)valine, 0.21 g of N-chlorosuccinimide and 3 ml of benzene is heated at reflux for 2 hours. The reaction is diluted with hexane, washed with water (2×) and solvent stripped to give the crude product. To the crude product is added 0.1 g of N-chlorosuccinimide and 3 ml benzene. The mixture is heated at reflux for 30 min and then allowed to stand overnight at RT. The reaction is worked up by diluting with hexane, washing with water and stripping off solvent to yield the m-phenoxybenzyl ester of N-(2,6-dimethyl-4-chlorophenyl)valine, MS m/e 437.1 (M+, 15.3).

Workup

  1. temperatureis heated
  2. temperatureat reflux for 2 hours
  3. washwashed with water (2×) and solvent
  4. customto give the crude product
  5. temperatureThe mixture is heated
  6. temperatureat reflux for 30 min
  7. washwashing with water

Sources & evidence

ORD record
ord-d39b5acdf9a14da09347d88c88086c21
Source dataset
uspto-grants-1983_10
Patent number
US04411912

Reaction notes

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