Sodium → HCID 178427408, compound

HRID 1249136Notes

Reaction equation

HRID 1249136 reaction equation
Br[CH2:2][N:3]1[C:7](=[O:8])[C:6]2=[CH:9][C:10]([NH:13][S:14]([C:17]3[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=3)(=[O:16])=[O:15])=[CH:11][CH:12]=[C:5]2[C:4]1=[O:24].[Na].[SH:26][C:27]1[N:31](C2C=CC=CC=2)[N:30]=[N:29][N:28]=1>O1CCCC1>[C:5]1([CH:2]([S:26][C:27]2[NH:31][N:30]=[N:29][N:28]=2)[N:3]2[C:7](=[O:8])[C:6]3=[CH:9][C:10]([NH:13][S:14]([C:17]4[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=4)(=[O:16])=[O:15])=[CH:11][CH:12]=[C:5]3[C:4]2=[O:24])[CH:6]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 5360545SodiumHCID 54505026HCID 54505026, compoundHCID 1785279861-phenyltetrazole-5-thiol

Product 1

HCID 178427408HCID 178427408, compoundYield 191.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

N-Bromomethyl-4-(p-toluenesulfonamido)phthalimide (13 g) was dissolved in tetrahydrofuran (200 ml) and thereto a tetrahydrofuran solution (100 ml) of the sodium salt of 5-mercapto-1-phenyltetrazole (6 g) was slowly added at room temperature. The reaction mixture was allowed to stand at room temperature for 2 hours. Thereafter, the reaction mixture was poured into ice-cold water, and the crystals precipitated were recovered by filtration to obtain a crude product. The thus obtained crude product was recrystallized from an ethyl acetate/methanol mixed solvent to yield 15.4 g of N-(1-phenyl-5-tetrazolylthiomethyl)-4-(p-toluenesulfonamido)phthalimide. Melting Point: 202°-204° C.

Workup

  1. additionThereafter, the reaction mixture was poured into ice-cold water
  2. customthe crystals precipitated
  3. filtrationwere recovered by filtration
  4. customto obtain a crude product
  5. customThe thus obtained crude product
  6. customwas recrystallized from an ethyl acetate/methanol mixed solvent

Sources & evidence

ORD record
ord-d057156370024724a5241231351496b1
Source dataset
uspto-grants-1986_12
Patent number
US04629683

Reaction notes

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