Water → 3,3-Dimethyl-5-(1-phenyl-1H-tetrazol-5-yloxy)-2,3dihydroisoindol-1-one

HRID 1737310Notes

Reaction equation

HRID 1737310 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[NH:6][C:5]2([CH3:13])[CH3:12].Cl[C:15]1[N:19]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:18]=[N:17][N:16]=1.C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[CH3:12][C:5]1([CH3:13])[C:4]2[C:8](=[CH:9][CH:10]=[C:2]([O:1][C:15]3[N:19]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[N:18]=[N:17][N:16]=3)[CH:3]=2)[C:7](=[O:11])[NH:6]1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 842621H-Tetrazole, 5-chloro-1-phenyl-HCID 107736505-Hydroxy-3,3-dimethylisoindolin-1-one

Product 1

HCID 218427183,3-Dimethyl-5-(1-phenyl-1H-tetrazol-5-yloxy)-2,3dihydroisoindol-1-oneYield 97%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of lactam 62 (1.77 g, 10.0 mmol) and 5-chloro-1phenyl-1H-tetrazole (2.17 g, 12.0 mmol) in dry DMF (50 mL) is treated with solid K2CO3 (2.07 g, 15.0 mmol). The mixture is stirred overnight at rt, then poured into water and extracted with EtOAc (2×). The organic phase is washed with water (3×) and brine (2×), then dried (MgSO4), filtered, and evaporated. The residue is crystallized from CH2Cl2 to give a white solid, mp 202-204° C. The material weighs 3.10 g (97% yield) . 1H NMR (CDCl3) 7.90 (d, 1, J=8.3), 7.80 (m, 2), 7.60-7.55 (m, 4), 7.50-7.45 (m, 1), 6.78 (s, 1), 1.59 (s, 6); 13C NMR (CDCl3) 168.45, 158.80, 156.15, 155.27, 132.83, 129.81, 128.77, 125.78, 122.33, 119.44, 112.11, 59.14, 53.39, 27.59; MS (MW=321.3, EI, eE=70 eV) m/z 321 (M+), 306, 293, 278, 261, 250, 236, 222, 208, 187, 176, 161 (base peak), 145, 133, 117, 103, 91, 77, 65, 42.

Workup

  1. extractionextracted with EtOAc (2×)
  2. washThe organic phase is washed with water (3×) and brine (2×)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue is crystallized from CH2Cl2
  7. customto give a white solid, mp 202-204° C

Sources & evidence

ORD record
ord-bac42e9c7d8a4f0a86a1541b52201602
Source dataset
uspto-grants-1999_10
Patent number
US05962469

Reaction notes

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