Ammonia → HCID 21507673, compound

HRID 1287291Notes

Reaction equation

HRID 1287291 reaction equation
CO[C:3](=[O:19])[C@H:4]([CH2:6][CH2:7][CH2:8][CH2:9][NH:10][C:11](=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[NH2:5].[CH3:20][N:21]=[C:22]=[S:23].N>C(O)C>[C:11]([NH:10][CH2:9][CH2:8][CH2:7][CH2:6][CH:4]1[NH:5][C:22](=[S:23])[N:21]([CH3:20])[C:3]1=[O:19])(=[O:18])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 11167Methyl isothiocyanateHCID 86734043HCID 86734043, compound

Product 1

HCID 21507673HCID 21507673, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
40 °C

Procedure

A solution of Nε-benzoyl-L-lysine methyl ester (26 g) and methyl isothiocyanate (6.75 g) in ethanol (250) was heated under reflux for 12 hours. The solution was saturated with ammonia at 0°C and heated in a bomb at 40°C for 3 days. Evaporation of the solvent gave a gum which was crystallised from isopropyl alcohol. Recrystallisation from iso-propyl alcohol gave the title compound as the quarter isopropyl alcohol solvate 10 g (m.p. 137-8°C). Found: C, 59.4; H, 6.25; N, 13.1. C15H19N3O2S.1/4C3H8O requires C, 59.0; H, 6.6; N, 13.1%.

Workup

  1. temperatureunder reflux for 12 hours
  2. customEvaporation of the solvent
  3. customgave a gum which
  4. customwas crystallised from isopropyl alcohol
  5. customRecrystallisation from iso-propyl alcohol

Sources & evidence

ORD record
ord-b972f7ff50fd425d80243ada77c552b5
Source dataset
uspto-grants-1976_10
Patent number
US03984430

Reaction notes

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