Hydrochloric Acid → 2-(Benzo[d]thiazol-2(3H)-ylidene)malononitrile

HRID 1091678Notes

Reaction equation

HRID 1091678 reaction equation
Cl[C:2]1[S:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.[C:11](#[N:15])[CH2:12][C:13]#[N:14].[O-]CC.[Na+].Cl>C(#N)C>[S:3]1[C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[NH:6][C:2]1=[C:12]([C:11]#[N:15])[C:13]#[N:14]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8010MalononitrileHCID 119872-ChlorobenzothiazoleHCID 2723922Sodium ethoxide

Product 1

HCID 6415632-(Benzo[d]thiazol-2(3H)-ylidene)malononitrileYield 47.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of 2-chlorobenzothiazole (1.0 mL, 8.1 mmol) and malononitrile (534 mg; 8.1 mmol) in acetonitrile (4 mL) was added sodium ethoxide (3.0 mL of 21 wt % solution in ethanol, 8.0 mmol). The mixture was stirred at room temperature for 4 d, then acidified with 2M hydrochloric acid. The solid was collected by filtration, washed with acetonitrile, and dried under vacuum to give 2-(benzothiazol-2(3H)-ylidene)malononitrile (770 mg) as a white solid.

Workup

  1. filtrationThe solid was collected by filtration
  2. washwashed with acetonitrile
  3. customdried under vacuum

Sources & evidence

ORD record
ord-f5177d7b64134f0eb4aad86d9c25b594
Source dataset
uspto-grants-2012_03
Patent number
US08129396B2

Reaction notes

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