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

HRID 1155637Notes

Reaction equation

HRID 1155637 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

4

Reactant 3

HCID 887Methanol2×HCID 10942334Sodium MethoxideHCID 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.

Workup

  1. customevaporated
  2. filtrationfiltered
  3. filtrationfiltered

Sources & evidence

ORD record
ord-09de33d89b3b4aebbff52ba5e9e59950
Source dataset
uspto-grants-1982_06
Patent number
US04332611

Reaction notes

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