Triethylamine → HCID 86735159, compound

HRID 973057Notes

Reaction equation

HRID 973057 reaction equation
[CH2:1]([O:3][C:4](=[O:11])[CH2:5][NH:6][CH2:7][CH:8]=[CH:9][Cl:10])[CH3:2].C(N(CC)CC)C.[Cl:19][CH2:20][CH2:21][CH2:22][C:23](Cl)=[O:24]>C1C=CC=CC=1>[CH2:1]([O:3][C:4](=[O:11])[CH2:5][N:6]([CH2:7][CH:8]=[CH:9][Cl:10])[C:23](=[O:24])[CH2:22][CH2:21][CH2:20][Cl:19])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 783704-Chlorobutyryl chlorideHCID 54043728HCID 54043728, compound

Product 1

HCID 86735159HCID 86735159, compoundYield 83.8%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
60 °C

Procedure

Into a 100 ml four-necked flask there were placed 17.8 g of N-(3-chloroallyl)glycine ethyl ester, 15.2 g of triethylamine and 50 ml of benzene, and then 16.9 g of γ-chlorobutyryl chloride was gradually dropwise added thereto at room temperature with thorough stirring. Thereafter, the mixture was stirred for 1 hour at 60° C. After cooling, the reaction solution was washed with water, the benzene layer was dried over anhydrous sodium sulfate and the benzene was removed under reduced pressure. The residue obtained was distilled under reduced pressure to obtain 23.7 g of the objective N-(3-chloroallyl)-N-γ-chlorobutyryl glycine ethyl ester (b.p.2 167 - 170° C, nD23.0 1.4884).

Workup

  1. customInto a 100 ml four-necked flask there were placed
  2. customat room temperature
  3. temperatureAfter cooling
  4. washthe reaction solution was washed with water
  5. dry with materialthe benzene layer was dried over anhydrous sodium sulfate
  6. customthe benzene was removed under reduced pressure
  7. customThe residue obtained
  8. distillationwas distilled under reduced pressure

Sources & evidence

ORD record
ord-90f57a94ef5d49eda773f547c70aa463
Source dataset
uspto-grants-1977_10
Patent number
US04054668

Reaction notes

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