Triethylamine → HCID 18975625, compound

HRID 2393327Notes

Reaction equation

HRID 2393327 reaction equation
[CH2:1]([NH:3][CH2:4][CH2:5][C:6]([OH:8])=[O:7])[CH3:2].[CH3:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([CH3:16])[C:11]=1[N:17]=[C:18]=[S:19].C(N(CC)CC)C>C(Cl)Cl>[CH3:16][C:12]1[CH:13]=[CH:14][CH:15]=[C:10]([CH3:9])[C:11]=1[NH:17][C:18](=[S:19])[N:3]([CH2:4][CH2:5][C:6]([OH:8])=[O:7])[CH2:1][CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 879762,6-Xylyl isothiocyanateHCID 12227201HCID 12227201, compound

Product 1

HCID 18975625HCID 18975625, compoundYield 39.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-ethylaminopropionic acid (19.8 g), 2,6-dimethylphenyl-isothiocyanate (16.3 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 formed was collected by filtration. Recrystallization from ethanol afforded the title compound (11 g) as a white solid, m.p. 115°-118° C.

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. customThe solid formed
  7. filtrationwas collected by filtration
  8. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-6625c77a72f04e8ea7be86a0aeae05ba
Source dataset
uspto-grants-1998_09
Patent number
US05807864

Reaction notes

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