HCID 21997642, compound → HCID 9859541, compound

HRID 1977120Notes

Reaction equation

HRID 1977120 reaction equation
[C:1]([CH2:3][S:4]([C:7]1[CH:12]=[C:11]([F:13])[CH:10]=[CH:9][C:8]=1[NH:14][C:15](=O)[CH3:16])(=[O:6])=[O:5])#[N:2]>[OH-].[Na+]>[F:13][C:11]1[CH:10]=[CH:9][C:8]2[NH:14][C:15]([CH3:16])=[C:3]([C:1]#[N:2])[S:4](=[O:6])(=[O:5])[C:7]=2[CH:12]=1

Participants

3

Reactant 1

HCID 21997642HCID 21997642, compound

Product 1

HCID 9859541HCID 9859541, compound

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
0 °C

Procedure

N-(2-Cyanomethylsulfonyl-4-fluoro-phenyl)acetamide (0.21 g) was dissolved in 0.5 M NaOH (3 ml) at room temperature. After 1½ h the mixture was filtered. The filtrate was cooled to 0° C. and 4M HCl (0.5 ml) was added. A white precipitate was isolated by filtration, washed with water (5 ml) and dried to give the title compound as a white solid. Yield 0.17 g (85%); mp 326-327° C. (decomp.); 1H-NMR (DMSO-d6), δ (ppm): 12.07 (s, 1H, NH), 7.95-7.81 (m, 1H, Ar—H), 7.75-7.45 (m, 2H, Ar—H), 2.47 (s, CH3 +DMSO); IR (KBr) ν (cm−1): 3291 (NH), 2214 (C≡N).

Workup

  1. filtrationAfter 1½ h the mixture was filtered
  2. addition4M HCl (0.5 ml) was added
  3. customA white precipitate was isolated by filtration
  4. washwashed with water (5 ml)
  5. customdried

Sources & evidence

ORD record
ord-b5cf5105666c48e8957d81ed53e1002d
Source dataset
uspto-grants-2001_05
Patent number
US06232310B1

Reaction notes

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