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

HRID 1712123Notes

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

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 (APCI, m/z): 221 [M+H]+.

Workup

filtrationfiltered
washThe solids were washed with ether
additionthe filtrated was diluted with an equal volume of hexane
filtrationfiltered
customThe combined solids were dried in vacuo

Sources & evidence

ORD record: ord-250cca50872441eebc48f4f94a9bd080
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07790902B2

Reaction notes

Loading…