Dimethylformamide → 2-Amino-5-cyanobenzene-1-sulfonamide

HRID 496123Notes

Reaction equation

HRID 496123 reaction equation
I[C:2]1[CH:3]=[CH:4][C:5]([NH2:12])=[C:6]([S:8]([NH2:11])(=[O:10])=[O:9])[CH:7]=1.C([O-])(O)=O.[Na+].[CH3:18][N:19](C=O)C>[C-]#N.[C-]#N.[Zn+2].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:18]([C:2]1[CH:3]=[CH:4][C:5]([NH2:12])=[C:6]([S:8]([NH2:11])(=[O:10])=[O:9])[CH:7]=1)#[N:19]

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 516892Sodium BicarbonateHCID 223240882-Amino-5-iodobenzenesulfonamide

Product 1

HCID 223239942-Amino-5-cyanobenzene-1-sulfonamideYield 92%

Reagents, catalysts & solvents 2

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
80 °C

Procedure

A mixture of 5-iodo-2-aminobenzene-sulfonamide (17.9 g; 60 mmol), Zn(CN)2 (4.9 g; 41.9 mmol) and Pd(PPh3)4 (2.5 g; 2.2 mmol) in DMF (150 ml) under N2 was heated to 80° C. for 2 h. The reaction mixture was poured into NaHCO3 (sat. aq., 600 ml) and extracted with EtOAc (9×200 ml). The combined organic fractions were washed with NaHCO3 (sat. aq.) and NaCl (sat. aq.), dried (Na2SO4), filtered and evaporated to dryness. The remanense was washed with water and hexane and filtered of to give 10.9 g (92%) of product.

Workup

  1. extractionextracted with EtOAc (9×200 ml)
  2. washThe combined organic fractions were washed with NaHCO3 (sat. aq.) and NaCl (sat. aq.)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated to dryness
  6. washThe remanense was washed with water and hexane
  7. filtrationfiltered of

Sources & evidence

ORD record
ord-f6dce26825324553a3fee2eed5589218
Source dataset
uspto-grants-2005_09
Patent number
US06943159B1

Reaction notes

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