Saccharin → HCID 86747126, compound

HRID 266444Notes

Reaction equation

HRID 266444 reaction equation
[Na].[S:2]1([C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:6](=[O:7])[NH:5]1)(=[O:4])=[O:3].[C:14]1([N:20]2[C:24](=[S:25])[N:23]([CH2:26]Cl)[N:22]=[N:21]2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CN(C=O)C>[C:14]1([N:20]2[C:24](=[S:25])[N:23]([CH2:26][N:5]3[C:6](=[O:7])[C:8]4[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=4)[S:2]3(=[O:3])=[O:4])[N:22]=[N:21]2)[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 5143SaccharinHCID 5360545SodiumHCID 15291093HCID 15291093, compound

Product 1

HCID 86747126HCID 86747126, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4.53 g (0.022 mol) of the sodium salt of saccharin and 5 g (0.022 mol) of 1-phenyl-4-chloromethyl-tetrazolin-5-thione in 50 ml of DMF was heated at 130° for four hours, then cooled and poured into ice water. The solid which separated was collected, washed with water, dried and chromatographed on silica gel, eluting with MDC, to give 4.8 g (58%) of 2-(1-phenyl-5-thioxotetrazolin-4-ylmethyl) saccharin, mp 140°-142° C.

Workup

  1. temperaturecooled
  2. customThe solid which separated
  3. customwas collected
  4. washwashed with water
  5. customdried
  6. customchromatographed on silica gel
  7. washeluting with MDC

Sources & evidence

ORD record
ord-c286d4decb4d4fb4916467d2274263e3
Source dataset
uspto-grants-1997_07
Patent number
US05650422

Reaction notes

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