Iodoethane → ethyl N-(m-chlorophenyl)-2-(2,6-dichlorophenyl)glycine

HRID 1389941Notes

Reaction equation

HRID 1389941 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][CH:9]([C:13]2[C:18]([Cl:19])=[CH:17][CH:16]=[CH:15][C:14]=2[Cl:20])[C:10]([OH:12])=[O:11])[CH:5]=[CH:6][CH:7]=1.CN(C)P(N(C)C)(N(C)C)=O.[H-].[Na+].[CH2:34](I)[CH3:35]>C1C=CC=CC=1>[CH2:34]([N:8]([C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=1)[CH:9]([C:13]1[C:18]([Cl:19])=[CH:17][CH:16]=[CH:15][C:14]=1[Cl:20])[C:10]([OH:12])=[O:11])[CH3:35]

Participants

6

Reactant 4

HCID 6340IodoethaneHCID 12679HexamethylphosphoramideHCID 24758Sodium hydrideHCID 20295986HCID 20295986, compound

Product 1

HCID 70568818ethyl N-(m-chlorophenyl)-2-(2,6-dichlorophenyl)glycine

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a stirred solution of 13.2 parts of N-(m-chlorophenyl)-2-(2,6-dichlorophenyl)glycine in 80 parts of hexamethylphosphoramide are added portionwise 2.1 parts of sodium hydride 50% and the whole is stirred for 30 minutes. Then there are added dropwise 6.9 parts of ethyl iodide and stirring is continued for 20 hours at room temperature. The reaction mixture is poured onto 320 parts of benzene. The organic layer is washed successively twice with 50 parts of water, twice with 50 parts of a sodium hydroxide solution 5% and again twice with 50 parts of water, dried, filtered and evaporated. The oily residue solidifies on standing at room temperature. The solid product is filtered off and crystallized from 2-propanol, yielding 8.9 parts of ethyl N-(m-chlorophenyl)-2-(2,6-dichlorophenyl)glycine; mp. 120.5° C.

Workup

  1. stirringstirring
  2. waitis continued for 20 hours at room temperature
  3. washThe organic layer is washed successively twice with 50 parts of water, twice with 50 parts of a sodium hydroxide solution 5% and again twice with 50 parts of water
  4. customdried
  5. filtrationfiltered
  6. customevaporated
  7. customon standing at room temperature
  8. filtrationThe solid product is filtered off
  9. customcrystallized from 2-propanol

Sources & evidence

ORD record
ord-0eb0381bf78048c58ff54c37d34198b9
Source dataset
uspto-grants-1981_01
Patent number
US04246429

Reaction notes

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