Methane → HCID 10220680, compound

HRID 1977104Notes

Reaction equation

HRID 1977104 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=O)[CH3:10])=[C:4]([S:12]([CH2:15][C:16]#[N:17])(=[O:14])=[O:13])[CH:3]=1.C>[OH-].[Na+]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]2[NH:8][C:9]([CH3:10])=[C:15]([C:16]#[N:17])[S:12](=[O:14])(=[O:13])[C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 297MethaneHCID 11208041HCID 11208041, compound

Product 1

HCID 10220680HCID 10220680, compoundYield 96.8%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
0 °C

Procedure

N-(4-Chloro-2-cyanomethylsulfonylphenyl)acetamide (0.73 g) was added at room temperature to 0.5 M aqueous NaOH (10 ml) to form a yellow solution. After 45 min 0.1 g of charcoal was added and the mixture was filtered through celite. The filtrate was cooled to 0° C. and 1 M HCl (7.5 ml) was added. After 30 min the precipitate was collected by filtration and dried to give 0.66 g of the title compound. Recrystallization from methanol gave pale crystals. Yield 0.45 g (66%); mp 297-299° C.; 1H-NMR(CD3OD) δ (ppm): 7.91 (d, J=2.8 Hz, 1H); 7.68 (dd, 1H); 7.37 (d, J=9 Hz, 1H); 4.88 (br, H2O+NH); 2.51 (s, 3H); 13C-NMR (DMSO-d6) δ (ppm): 155.9, 134, 133.9, 129.6, 125.0, 121.40, 121.36, 112.7, 85.7, 20.3. IR (KBr) ν (cm−1): 3259, 3176, 3100, 2214, 1531, 1482, 1305, 1144. An additional crop of the title compound (0.09 g, 13%) was obtained from the mother liqueor.

Workup

  1. customto form a yellow solution
  2. filtrationthe mixture was filtered through celite
  3. addition1 M HCl (7.5 ml) was added
  4. filtrationAfter 30 min the precipitate was collected by filtration
  5. customdried

Sources & evidence

ORD record
ord-9bdc45e579a74bffad0d3ad58a1893f3
Source dataset
uspto-grants-2001_05
Patent number
US06232310B1

Reaction notes

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