Sodium Hydroxide → HCID 22492410, compound

HRID 351082Notes

Reaction equation

HRID 351082 reaction equation
C[O:2][C:3](=[O:24])/[CH:4]=[CH:5]/[C:6]#[C:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([S:14](=[O:23])(=[O:22])[NH:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:9]=1.[OH-].[Na+]>CO>[C:16]1([NH:15][S:14]([C:10]2[CH:9]=[C:8]([C:7]#[C:6]/[CH:5]=[CH:4]/[C:3]([OH:24])=[O:2])[CH:13]=[CH:12][CH:11]=2)(=[O:23])=[O:22])[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 20780487HCID 20780487, compound

Product 1

HCID 22492410HCID 22492410, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of E-5-(3-phenylsulfamoylphenyl)pent-2-en-4-ynoic acid methyl ester (55a) (0.34 g, 1 mmol) in methanol (3 ml) 1N solution of sodium hydroxide (3 ml) was added and the mixture was stirred at ambient temperature for 3 hours. Methanol was removed under reduced pressure, to the residue water (5 ml) was added and the mixture was acidified with 3% HCl. The precipitate was filtered, washed with water, and dried to give the title compound (0.31 g, 95%) as white crystals. M.p. 188–190° C. 1H NMR (DMSO-d6, HMDSO) δ: 6.36 (1H, d, J=15.8 Hz, CH); 6.92 (1H, d, J=15.8 Hz, CH); 7.01–7.36 (5H, m, C6H5); 7.38–7.89 (4H, m, C6H4); 10.32 (1H, s, NH).

Workup

  1. customMethanol was removed under reduced pressure, to the residue water (5 ml)
  2. additionwas added
  3. filtrationThe precipitate was filtered
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-6d29323e9efd410bae08902f67ec4f4c
Source dataset
uspto-grants-2007_02
Patent number
US07183298B2

Reaction notes

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