Sodium → HCID 178515058, compound

HRID 266443Notes

Reaction equation

HRID 266443 reaction equation
[C:1]1([CH:7](Cl)[N:8]2[C:18](=[O:19])[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[S:9]2(=[O:11])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Na].C1([N:28]2[C:32]([SH:33])=[N:31][N:30]=[N:29]2)C=CC=CC=1>CN(C=O)C>[C:1]1([C:1]2([CH:7]([S:33][C:32]3[NH:31][N:30]=[N:29][N:28]=3)[N:8]3[C:18](=[O:19])[C:17]4[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=4)[S:9]3(=[O:10])=[O:11])[CH:2]=[CH:3][CH:4]=[CH:5][CH2:6]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 5360545SodiumHCID 70050420HCID 70050420, compoundHCID 1785279861-phenyltetrazole-5-thiol

Product 1

HCID 178515058HCID 178515058, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2.2 g (0.0071 mol) of 2-(phenyl-chloromethyl)saccharin and 1.4 g (0.0071 mol) of the sodium salt of 1-phenyl-5-mercaptotetrazole in 30 ml of DMF was heated at 55° for three and one half hours, then stirred at ambient temperature for about sixteen hours and poured into ice water containing dilute sodium bicarbonate. The solid which separated was collected, washed with water, air dried and chromatographed on silica gel, eluting with 98:2 MDC: diethyl ether, to give 2 g (63%) of 2-(1-phenyl-1H-tetrazol-5-ylthiophenylmethyl) saccharin, mp 192°-193 ° C.

Workup

  1. customThe solid which separated
  2. customwas collected
  3. washwashed with water, air
  4. customdried
  5. customchromatographed on silica gel
  6. washeluting with 98:2 MDC

Sources & evidence

ORD record
ord-f5c7c678997d453a8ebbe90e32bc4607
Source dataset
uspto-grants-1997_07
Patent number
US05650422

Reaction notes

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