Triethylamine → HCID 18975633, compound

HRID 2393331Notes

Reaction equation

HRID 2393331 reaction equation
[CH2:1]([NH:4][CH2:5][CH2:6][C:7]([OH:9])=[O:8])[CH:2]=[CH2:3].[CH3:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([CH3:17])[C:12]=1[N:18]=[C:19]=[S:20].C(N(CC)CC)C>C(Cl)Cl>[CH2:1]([N:4]([CH2:5][CH2:6][C:7]([OH:9])=[O:8])[C:19]([NH:18][C:12]1[C:11]([CH3:10])=[CH:16][CH:15]=[CH:14][C:13]=1[CH3:17])=[S:20])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 879762,6-Xylyl isothiocyanateHCID 14093037HCID 14093037, compound

Product 1

HCID 18975633HCID 18975633, compoundYield 39.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of the 3-allylaminopropionic acid (21.9 g), 2,6-dimethylphenyl-isothiocyanate (19 g), triethylamine (20 g) and methylene chloride (200 mL) was heated at reflux for 3 hours. The cooled reaction mixture was extracted with 1N NaOH (150 mL). The aqueous layer was separated and acidified with 2N HCl. The solid was collected by filtration. 13.5 g of the title compound was obtained and used without further purification for the reaction in step 3.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3 hours
  3. customThe cooled reaction mixture
  4. extractionwas extracted with 1N NaOH (150 mL)
  5. customThe aqueous layer was separated
  6. filtrationThe solid was collected by filtration

Sources & evidence

ORD record
ord-32e05f524b7a458d9d097b49a47b4634
Source dataset
uspto-grants-1998_09
Patent number
US05807864

Reaction notes

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