Formaldehyde → 2-Hydroxymethyl-4-methylsaccharin

HRID 266430Notes

Reaction equation

HRID 266430 reaction equation
[CH3:1][C:2]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:3]=1[C:4](=[O:13])[NH:5][S:6]2(=[O:8])=[O:7].[CH2:14]=[O:15]>C(O)C>[OH:15][CH2:14][N:5]1[C:4](=[O:13])[C:3]2[C:9](=[CH:10][CH:11]=[CH:12][C:2]=2[CH3:1])[S:6]1(=[O:8])=[O:7]

Participants

4

Reactant 2

HCID 712FormaldehydeHCID 159340754-Methyl-1H-1lambda~6~,2-benzothiazole-1,1,3(2H)-trione

Product 1

HCID 152250552-Hydroxymethyl-4-methylsaccharinYield 82%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-Methylsaccharin prepared in (b) (500 mg; 2.54 mmol) was dissolved in 2.53 ml of warm ethanol (steam bath). Once a homogeneous solution was achieved, formalin (37% in methanol; 1.76 ml excess) was added dropwise. The solution was allowed to cool to room temperature and then chilled to 0° C. for 4 days. The resulting solid was collected and air-dried to afford 476 mg (82%) of 2-hydroxymethyl-4-methylsaccharin, mp 196°-198° C. 1H nmr (300 MHz, CDCl3): 7.767 (1H, t, J=6.75 Hz); 7.732 (1H, d, J=7.72 Hz); 7.600 (1H, d, J=6.64 Hz); 5.361 (2H, d, J-8.00 Hz); 3.296 (1H, t, J=8.16 Hz); 2.793 (3H, s). IR (KBr, cm1): 3505 (s); 3070 (w); 1735 (s); 1580 (m).

Workup

  1. temperaturechilled to 0° C. for 4 days
  2. customThe resulting solid was collected
  3. customair-dried

Sources & evidence

ORD record
ord-b9e22fcfbeab4c0286386112b06f9a53
Source dataset
uspto-grants-1997_07
Patent number
US05650422

Reaction notes

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