Methanol → 2-(Hydroxymethyl)-N-[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]benzenesulfonamide

Reaction equation

C([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[S:12]([NH:15][C:16]([NH:18][C:19]1[N:24]=[C:23](Cl)[N:22]=[C:21](Cl)[N:20]=1)=[O:17])(=[O:14])=[O:13])(=O)C.[CH3:27][O-:28].[Na+].[CH3:30][OH:31]>>[OH:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[S:12]([NH:15][C:16]([NH:18][C:19]1[N:20]=[C:21]([O:28][CH3:27])[N:22]=[C:23]([O:31][CH3:30])[N:24]=1)=[O:17])(=[O:13])=[O:14]

Participants

Reactant 3

HCID 887Methanol2×

HCID 10942334Sodium Methoxide

HCID 205372422-(acetoxymethyl)-N-[(4,6-dichloro-1,3,5-triazinyl)aminocarbonyl]benzenesulfonamide

Product 1

HCID 130973002-(Hydroxymethyl)-N-[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]benzenesulfonamide

Procedure

The crude 2-(acetoxymethyl)-N-[(4,6-dichloro-1,3,5-triazinyl)aminocarbonyl]benzenesulfonamide was treated with methanol (10 ml) and then with a solution of sodium methoxide (14 mmol) in methanol. The mixture was stirred at room temperature for 1.5 hour and evaporated. The residue was taken up in water and filtered. The filtrate was acidified and filtered to give 0.45 g of gummy solid which was recrystallized from a chloroform/acetone mixture to give 115 mg of white solid, m.p. 146°-148°(dec.). 'H NMR δDMSO-d6 12.2(brd s, 1H), 10.73 (s, 1H), 8.00-7.15 (m,4H), 4.80 (s and ~4.9-4.2 (brd s), 3H) 3.90 (s, 6H), consistent with the assigned structure.