Water → HCID 22791110, compound

HRID 1658587Notes

Reaction equation

HRID 1658587 reaction equation
[OH-].[NH4+].O.[C:4]([NH:7][C@H:8]([C:11]([OH:13])=[O:12])[CH2:9][SH:10])(=[O:6])[CH3:5]>C(O)(C)C>[NH4+:7].[C:4]([NH:7][C@H:8]([C:11]([O-:13])=[O:12])[CH2:9][SH:10])(=[O:6])[CH3:5]

Participants

5

Reactant 3

HCID 962WaterHCID 12035N-Acetyl-L-CysteineHCID 14923Ammonium Hydroxide

Product 1

HCID 22791110HCID 22791110, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
35 °C

Procedure

A solution of concentrated ammonium hydroxide (52 ml., 0.78 mole) and 20 ml. water is added in 10 minutes to a stirred mixture of N-acetyl-L-cysteine (114.2 g., 0.7 mole) in 1.2 liters of isopropanol under an atmosphere of nitrogen. During the addition the mixture thickens and the temperature increases to 35°C. The mixture is stirred overnight, collected and washed with isopropanol to yield 110 g. (87%) of product having a melting point of 156°-158°C. (dec.) (uncorr.). Crystallization of this product from water-isopropanol with cooling to -10°C. provides analytically pure N-acetyl-L-cysteine ammonium salt, M.P. 147.5°-150°C. (dec.) (corr.); [ α ]D25 + 20.6°(c 5,H2O).

Workup

  1. additionDuring the addition the mixture thickens
  2. customcollected
  3. washwashed with isopropanol
  4. customto yield 110 g
  5. customCrystallization of this product from water-isopropanol
  6. temperaturewith cooling to -10°C.

Sources & evidence

ORD record
ord-e2f5d8fa9eb94027a38dbb2465448e45
Source dataset
uspto-grants-1976_06
Patent number
US03965167

Reaction notes

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