Acetic Acid → 2-(4-Phenylthiazol-2-yl)malononitrile

HRID 630689Notes

Reaction equation

HRID 630689 reaction equation
O=[C:2]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH2:3][S:4][C:5]#[N:6].[C:13](#[N:17])[CH2:14][C:15]#[N:16].C(N(CC)CC)C.C(O)(=O)C>C(O)C.O>[C:7]1([C:2]2[N:6]=[C:5]([CH:14]([C:13]#[N:17])[C:15]#[N:16])[S:4][CH:3]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 8010MalononitrileHCID 8471TriethylamineHCID 219693Phenacyl thiocyanate

Product 1

HCID 122636142-(4-Phenylthiazol-2-yl)malononitrileYield 87.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

In a 100 mL three-neck flask, 10.0 g (56.4 mmol) of 2-oxo-2-phenylethyl thiocyanate and 3.73 g (56.4 mmol) of malononitrile were dissolved in 60 mL of ethanol and admixed with 5.14. g (50.8 mmol) of triethylamine in a gradual manner, so the temperature did not climb above 30° C. This was followed by stirring at room temperature for 12 h. The reaction mixture was diluted with 50 mL of water and acidified with glacial acetic acid. The precipitated solid was separated off and washed three times with 10 mL of a 10:10:1 mixture of water:ethanol:glacial acetic acid each time. The solid was dried to obtain 11.1 g (49.1 mmol) of (4-phenyl-1,3-thiazol-2-yl)malononitrile.

Workup

  1. customdid not climb above 30° C
  2. customThe precipitated solid was separated off
  3. washwashed three times
  4. additionwith 10 mL of a 10:10:1 mixture of water
  5. customThe solid was dried

Sources & evidence

ORD record
ord-62b8b166c2fa4adbb1c6edf9c2a84d98
Source dataset
uspto-grants-2016_04
Patent number
US09317012B2

Reaction notes

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