Water → 1H-Isoindole-1,3(2H)-dione, 2-[[(1-phenyl-1H-tetrazol-5-yl)thio]methyl]-

HRID 1703046Notes

Reaction equation

HRID 1703046 reaction equation
Br[CH2:2][N:3]1[C:7](=[O:8])[C:6]2=[CH:9][CH:10]=[CH:11][CH:12]=[C:5]2[C:4]1=[O:13].[C:14]1([N:20]2[C:24]([SH:25])=[N:23][N:22]=[N:21]2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[Na].O>CN(C)C(=O)C>[C:7]1(=[O:8])[N:3]([CH2:2][S:25][C:24]2[N:20]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[N:21]=[N:22][N:23]=2)[C:4](=[O:13])[C:5]2=[CH:12][CH:11]=[CH:10][CH:9]=[C:6]12

Participants

6

Reactant 4

HCID 962WaterHCID 792441H-Isoindole-1,3(2H)-dione, 2-(bromomethyl)-HCID 5360545SodiumHCID 1785279861-phenyltetrazole-5-thiol

Product 1

HCID 7974791H-Isoindole-1,3(2H)-dione, 2-[[(1-phenyl-1H-tetrazol-5-yl)thio]methyl]-Yield 72%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

A solution of 2.40 g N-(bromomethyl)phthalimide (0.010 mol) and 2.00 g 1-phenyl-1H-tetrazole-5-thiol, sodium salt (0.010 mol) in 20 ml N,N-dimethylacetamide was stirred 0.5 hours. The slurry was then poured into water extracted with ethyl acetate, dried and concentrated in vacuo. The solid obtained was recrystallized from ethyl acetate/hexane to give 2.43 g (72.0%) of a colorless solid, m.p. 146°-7° C.

Workup

  1. extractionextracted with ethyl acetate
  2. customdried
  3. concentrationconcentrated in vacuo
  4. customThe solid obtained
  5. customwas recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-619dc7fd0274491b8753043491d1167b
Source dataset
uspto-grants-1982_09
Patent number
US04350752

Reaction notes

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