Hydrazine → HCID 21886092, compound

HRID 723142Notes

Reaction equation

HRID 723142 reaction equation
[C:1]([N:20]1[N:24]=[N:23][C:22]([CH2:25][CH2:26][CH2:27][CH2:28][N:29]2C(=O)C3C(=CC=CC=3)C2=O)=[N:21]1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.NN>CC(O)C.C1COCC1>[C:1]([N:20]1[N:24]=[N:23][C:22]([CH2:25][CH2:26][CH2:27][CH2:28][NH2:29])=[N:21]1)([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 21886526HCID 21886526, compound

Product 1

HCID 21886092HCID 21886092, compoundYield 109.1%

Reagents, catalysts & solvents 1

HCID 22597222Tetrahydrofuran 2-propanolSolvent

Procedure

To a solution of 2-[4-(2-trityl-2H-tetrazol-5-yl)-butyl]-isoindole-1,3-dione (175 mg, 0.313 mmol) in 2-propanol/THF (2:1, 3.0 mL) was added hydrazine (30 mL, 0.939 mmol). The solution was stirred at ambient temperature for 16 h. White solid was filtered off and washed with DCM (5×). The filtrate and the washings were combined, concentrated, dissolved in DCM, washed with H2O (2×) and brine, dried over Na2SO4, and concentrated to give the title compound (131 mg, 97% yield) as a pale yellow oil.

Workup

  1. filtrationWhite solid was filtered off
  2. washwashed with DCM (5×)
  3. concentrationconcentrated
  4. dissolutiondissolved in DCM
  5. washwashed with H2O (2×) and brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-519b643508a645d382b70ec39a85ec35
Source dataset
uspto-grants-2006_11
Patent number
US07138530B2

Reaction notes

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