Ethanol → HCID 15009009, compound

HRID 981069Notes

Reaction equation

HRID 981069 reaction equation
[OH-].[Na+].[C:3]([S:6][CH2:7][C:8]1[NH:9][C:10](=[O:13])[S:11][CH:12]=1)(=O)N.C(O)C.[C:17](#[N:20])[CH:18]=C>O.C(O)(=O)C>[C:17]([CH2:18][CH2:3][S:6][CH2:7][C:8]1[NH:9][C:10](=[O:13])[S:11][CH:12]=1)#[N:20]

Participants

7

Reactant 4

HCID 702EthanolHCID 7855AcrylonitrileHCID 14798Sodium HydroxideHCID 15009008HCID 15009008, compound

Product 1

HCID 15009009HCID 15009009, compoundYield 76.5%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

60 ml (0.60 mol) of 10N sodium hydroxide solution are added dropwise to a suspension containing 57 g (0.30 mol) of 4-carbamoylmercaptomethyl-2(3H)-thiazolone [compound of the formula (Ib)] in 150 ml of water and 90 ml of ethanol under stirring while bubbling an inert gas through the mixture. After 5 minutes, 17.5 g (0.33 mol) of acrylnitrile are added dropwise to the resulting solution at 25° to 30° C. The mixture is stirred for an additional 4 hours, then filtered to obtain a sharply clear solution which is then acidified by adding 27 ml of glacial acetic acid. The crystalline precipitate is filtered off at 15° to 20° C., washed with water and then with isopropanol and dried to give 45.8 g (76.5%) of the named compound, m.p.: 108°-111° C. The active ingredient content of the substance is 99.6%.

Workup

  1. customwhile bubbling an inert gas through the mixture
  2. filtrationfiltered
  3. customto obtain a sharply clear solution which
  4. filtrationThe crystalline precipitate is filtered off at 15° to 20° C.
  5. washwashed with water
  6. dry with materialwith isopropanol and dried

Sources & evidence

ORD record
ord-fb8caefb07814d52b87a86de4940781c
Source dataset
uspto-grants-1991_02
Patent number
US04990524

Reaction notes

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