Malononitrile → 2-Cyano-thioacetimidic acid 4-methoxy-benzyl ester

HRID 750560Notes

Reaction equation

HRID 750560 reaction equation
[OH-].[Na+].[CH3:3][O:4][C:5]1[CH:12]=[CH:11][C:8]([CH2:9][SH:10])=[CH:7][CH:6]=1.[C:13](#[N:17])[CH2:14][C:15]#[N:16]>C(O)C.O.[NH4+].[Cl-].O>[CH3:3][O:4][C:5]1[CH:12]=[CH:11][C:8]([CH2:9][S:10][C:13](=[NH:17])[CH2:14][C:15]#[N:16])=[CH:7][CH:6]=1

Participants

7

Reactant 3

HCID 8010MalononitrileHCID 14798Sodium HydroxideHCID 804074-Methoxy-alpha-toluenethiol

Product 1

HCID 205771932-Cyano-thioacetimidic acid 4-methoxy-benzyl esterYield 60.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 25517Ammonium ChlorideSolventHCID 19096565Water ethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of sodium hydroxide (13 g, 0.32 mol) in 750 mL of 1:1 ethanol-water at 0° C. was added 4-methoxybenzylmercaptan (50 g, 0.324 mol) and malononitrile (21 g, 0.324 mol). After stirring for 3 hours at 0° C., the mixture was diluted with 500 mL of saturated aqueous NH4Cl, diluted with 4 l of water and filtered. The solids were washed with ether, and the filtrated was diluted with an equal volume of hexane and filtered. The combined solids were dried in vacuo, affording 43 g (60%) of 2-cyano-thioacetimidic acid 4-methoxy-benzyl ester as a colorless solid. 1H NMR (400 MHz, CDCl3) δ 7.22 (d, 2H, J=7.6 Hz), 6.84 (d, 2H, J=8.8 Hz), 4.74 (bs, 1H), 3.98 (s, 2H), 3.78 (s, 3H) ppm; MS (APCl, m/z): 221 [M+H]+.

Workup

  1. filtrationfiltered
  2. washThe solids were washed with ether
  3. additionthe filtrated was diluted with an equal volume of hexane
  4. filtrationfiltered
  5. customThe combined solids were dried in vacuo

Sources & evidence

ORD record
ord-ee2ad3d4432843aaad94a8a008a8face
Source dataset
uspto-grants-2008_07
Patent number
US07405218B2

Reaction notes

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