HCID 70050498, compound → HCID 70053097, compound

HRID 266478Notes

Reaction equation

HRID 266478 reaction equation
Cl[CH2:2][N:3]1[C:13](=[O:14])[C:12]2[C:7](=[C:8]([O:21][CH3:22])[C:9]([CH2:18][CH2:19][CH3:20])=[CH:10][C:11]=2[O:15][CH2:16][CH3:17])[S:4]1(=[O:6])=[O:5].[Na].[C:24]1([N:30]2[C:34]([SH:35])=[N:33][N:32]=[N:31]2)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>>[C:24]1([N:30]2[C:34]([S:35][CH2:2][N:3]3[C:13](=[O:14])[C:12]4[C:7](=[C:8]([O:21][CH3:22])[C:9]([CH2:18][CH2:19][CH3:20])=[CH:10][C:11]=4[O:15][CH2:16][CH3:17])[S:4]3(=[O:6])=[O:5])=[N:33][N:32]=[N:31]2)[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

3

Reactant 2

HCID 70050498HCID 70050498, compoundHCID 178527989HCID 178527989, compound

Product 1

HCID 70053097HCID 70053097, compoundYield 71%

Procedure

By the method of part F of Example 45 condensation of 2-chloromethyl-4-ethoxy-6-propyl-7-methoxysaccharin (0.62 g) and 1-phenyltetrazol-5-thiol sodium salt (0.36 g initially and a small amount more after 3.5 hours reaction time, total reaction time 8 hours) and isolation of the oily product by extraction with dichloromethane and purification thereof first by column chromatography on silica gel using dichloromethane as eluant and then by crystallization of the resulting oil (0.62 g., 71% yield) from ethanol gave 2-(1-phenyltetrazol-5-yl)thiomethyl-4-ethoxy-6-propyl-7-methoxysaccharin, mp 110°-111° C.

Workup

  1. customa small amount more after 3.5 hours reaction time, total reaction time 8 hours) and isolation of the oily product
  2. extractionby extraction
  3. customwith dichloromethane and purification
  4. customby crystallization of the resulting oil (0.62 g., 71% yield) from ethanol

Sources & evidence

ORD record
ord-a93f2e193aca42b3bfb624dc0c4b2faf
Source dataset
uspto-grants-1997_07
Patent number
US05650422

Reaction notes

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