Hydrochloric Acid → 2-Cyanomethylbenzothiazole-6-sulfonic acid amide

HRID 407293Notes

Reaction equation

HRID 407293 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH2:11])(=[O:10])=[O:9])=[CH:4][C:3]=1[SH:12].[C:13](#N)[CH2:14][C:15]#[N:16].Cl>C(O)C>[C:15]([CH2:14][C:13]1[S:12][C:3]2[CH:4]=[C:5]([S:8]([NH2:11])(=[O:9])=[O:10])[CH:6]=[CH:7][C:2]=2[N:1]=1)#[N:16]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8010MalononitrileHCID 66767970HCID 66767970, compound

Product 1

HCID 667682562-Cyanomethylbenzothiazole-6-sulfonic acid amideYield 22.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 4-amino-3-mercaptobenzenesulfonamide (74 g, 208 mmol) and malononitrile (25 g, 375 mmol) in 650 mL of ethanol with 1.3 mL of conc. HCl was refluxed under argon overnight. The dark brown solids were isolated by filtration and were washed with ethanol and ether to yield approximately 30 g of the crude product. The volume of the filtrate was reduced by evaporation and the solids that precipitated were isolated by filtration to yield an additional 12 g of product. The crude material was purified by flash column chromatography eluting with CH2Cl2:MeOH:ammonia (60:20:1 mL) to yield a total of 22.2 g (35% for three steps) of the title compound as an orange powder.

Workup

  1. temperaturewas refluxed under argon overnight
  2. customThe dark brown solids were isolated by filtration
  3. washwere washed with ethanol and ether
  4. customto yield approximately 30 g of the crude product
  5. customThe volume of the filtrate was reduced by evaporation
  6. customthe solids that precipitated
  7. customwere isolated by filtration

Sources & evidence

ORD record
ord-0d50fd8c2b764bebb6356bd27b0fdd4e
Source dataset
uspto-grants-2014_06
Patent number
US08754233B2

Reaction notes

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