HCID 3395917, compound → HCID 13785816, compound

HRID 2309278Notes

Reaction equation

HRID 2309278 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[S:11]([N:14]([CH2:16][C:17]#[N:18])[CH3:15])(=[O:13])=[O:12])(OC)=[O:2].C[O-].[Na+].CO>C1(C)C=CC=CC=1>[C:17]([C:16]1[N:14]([CH3:15])[S:11](=[O:13])(=[O:12])[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[C:1]=1[OH:2])#[N:18]

Participants

4

Reactant 2

HCID 3395917HCID 3395917, compoundHCID 23694274Sodium methanolate methanol

Product 1

HCID 13785816HCID 13785816, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of o-carbomethoxy-N-cyanomethyl-N-methylbenzenesulfonamide (108 g) in toluene (600 ml) was added 28% sodium methoxide-methanol solution (83 ml) with vigorous stirring. After 2 hours the solvent was evaporated to ca. 400 ml and water (800 ml) added to dissolve the viscous residue. The pH was adjusted to ca. 2 with 6N HCl. The resulting crystals were granulated for 1 hour, filtered off, washed with water and dried in vacuo to give the title product, 77.2 g (81.1%). Purified product was obtained in 75% yield by dissolving the compound (3.3 g) in isopropanol, followed by dropwise addition of water (35 ml).

Workup

  1. customAfter 2 hours the solvent was evaporated to ca. 400 ml and water (800 ml)
  2. additionadded
  3. dissolutionto dissolve the viscous residue
  4. filtrationfiltered off
  5. washwashed with water
  6. customdried in vacuo

Sources & evidence

ORD record
ord-12d1d1f333554d3ea0b35f7d396bbc50
Source dataset
uspto-grants-1987_09
Patent number
US04694080

Reaction notes

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