Ethylamine → HCID 3980699, compound

HRID 1579541Notes

Reaction equation

HRID 1579541 reaction equation
[S:1]([NH:11][CH:12]([C:14](Cl)=[O:15])[CH3:13])([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].[CH2:17]([NH2:19])[CH3:18]>ClCCl>[CH2:17]([NH:19][C:14](=[O:15])[CH:12]([CH3:13])[NH:11][S:1]([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2])[CH3:18]

Participants

4

Reactant 2

HCID 6341EthylamineHCID 12924679tosyl-DL-alanyl chloride

Product 1

HCID 3980699HCID 3980699, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 125 grams of tosyl-DL-alanyl chloride (A. F. Beecham, J. Am. Chem. Soc., 79, 325-7) in 800 ml. of dichloromethane was added with stirring to 73 grams of anhydrous ethylamine and 400 ml. of dichloromethane in a reaction flask equipped with a dry ice condenser. The mixture was refluxed 4 hours after addition was completed. The reaction mixture was extracted with water then dried over magnesium sulfate. The solvent was removed in vacuo. The residue was slurried with diethyl ether and filtered to obtain tosyl-DL-alanine ethylamide, m.p. 106°-107°C.

Workup

  1. temperatureThe mixture was refluxed 4 hours
  2. additionafter addition
  3. extractionThe reaction mixture was extracted with water
  4. dry with materialthen dried over magnesium sulfate
  5. customThe solvent was removed in vacuo
  6. filtrationfiltered

Sources & evidence

ORD record
ord-aba8f775384b437ab7ea10c34ae6f19c
Source dataset
uspto-grants-1976_01
Patent number
US03931218

Reaction notes

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