Formaldehyde → 2-Hydroxymethyl-4-chlorosaccharin

HRID 266433Notes

Reaction equation

HRID 266433 reaction equation
[OH:1][CH2:2][N:3]1[C:13](=[O:14])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2C)[S:4]1(=[O:6])=[O:5].[Cl:16]C1C=CC=C2C=1C(=O)NS2(=O)=O.C=O>>[OH:1][CH2:2][N:3]1[C:13](=[O:14])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[Cl:16])[S:4]1(=[O:6])=[O:5]

Participants

4

Reactant 3

HCID 712FormaldehydeHCID 152250552-Hydroxymethyl-4-methylsaccharinHCID 155671714-Chloro-2,3-dihydro-1lambda6,2-benzothiazole-1,1,3-trione

Product 1

HCID 700447212-Hydroxymethyl-4-chlorosaccharin

Procedure

2-Hydroxymethyl-4-chlorosaccharin was prepared in the same manner as 2-hydroxymethyl-4-methylsaccharin, in Example 1, from 4-chlorosaccharin (1.00 g; 4.60 mmol) and formalin (37%; 3.22 ml; excess). All attempts to crystallize the viscous oily product resulted in decomposition to the starting material, and the product was thus used in the next step without characterization.

Workup

  1. customAll attempts to crystallize the viscous oily product
  2. customresulted in decomposition to the starting material

Sources & evidence

ORD record
ord-470d939b1cef40f69bf870ddc61596c3
Source dataset
uspto-grants-1997_07
Patent number
US05650422

Reaction notes

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