Sodium hydride → HCID 11208041, compound

HRID 1977103Notes

Reaction equation

HRID 1977103 reaction equation
[H-].[Na+].[C:3]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][C:8]=1[S:14]([OH:16])=[O:15])(=[O:5])[CH3:4].I[CH2:18][C:19]#[N:20]>CN(C)C=O>[Cl:13][C:10]1[CH:11]=[CH:12][C:7]([NH:6][C:3](=[O:5])[CH3:4])=[C:8]([S:14]([CH2:18][C:19]#[N:20])(=[O:16])=[O:15])[CH:9]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 69356IodoacetonitrileHCID 11356734HCID 11356734, compound

Product 1

HCID 11208041HCID 11208041, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

Sodium hydride (0.10 g, 60% dispersion in mineral oil) was added at ambient temperature under nitrogen in small portions to a stirred solution of 2-acetylamino-5-chloro-benzenesulfinic acid (0.55 g) in dry dimethylformamide. After stirring for 35 min iodoacetonitrile (0.18 ml) was added and the temperature was raised to 70° C. for 45 min. Then the solvent was removed in vacuo. The residue was triturated with water (30 ml) and filtered. The filter cake was dried, stirred with a mixture of ether (5 ml) and petroleum ether (10 ml) for 1 h, filtered off and dried to give the title compound as white needles. Yield 0.52 g (81%), mp 173.5-174° C., 1H-NMR(DMSO-d6) δ (ppm): 9.69 (s, 1H); 8.06-7.87 (m, 3H); 5.37 (s, 2H), 2.16 (s, 3H); 13C-NMR (DMSO-d6) δ (ppm): 169.6, 136.6, 136.4, 130.5, 129.8, 129.5, 128.5, 112.0, 44.9, 24.3; IR(KBr) ν (cm−1): 3343(NH), 2258(CN), 1682(C═O), 1330(SO2), 1156 and 1140 (SO2).

Workup

  1. additionwas added
  2. customThen the solvent was removed in vacuo
  3. customThe residue was triturated with water (30 ml)
  4. filtrationfiltered
  5. customThe filter cake was dried
  6. filtrationfiltered off
  7. customdried

Sources & evidence

ORD record
ord-87045df217094662b1befd207d1df1cb
Source dataset
uspto-grants-2001_05
Patent number
US06232310B1

Reaction notes

Loading…