Acetic Anhydride → Acetate

HRID 638591Notes

Reaction equation

HRID 638591 reaction equation
[C:1]1([C:7]2[N:12]3[N:13]=[N:14][N:15]=[C:11]3[N:10]3[N:16]=[CH:17][N:18]=[C:9]3[C:8]=2[CH2:19][CH2:20][OH:21])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:22]([O:25]C(=O)C)(=[O:24])[CH3:23]>N1C=CC=CC=1>[C:1]1([C:7]2[N:12]3[N:13]=[N:14][N:15]=[C:11]3[N:10]3[N:16]=[CH:17][N:18]=[C:9]3[C:8]=2[CH2:19][CH2:20][OH:21])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1.[C:22]([O-:25])(=[O:24])[CH3:23]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 13559527HCID 13559527, compound

Product 2

HCID 175AcetateHCID 13559527HCID 13559527, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution containing 2.8 g of 5-phenyltetrazolo[1,5-a][1,2,4]triazolo[1,5-c]pyrimidine-6-ethanol (0.01 mole) dissolved in 15 ml of pyridine is added 1.5 ml of acetic anhydride (0.015 mole). The reaction mixture is maintained at room temperature for 48 hours and then is evaporated to dryness yielding a crude product. The crude product is chromatographed on silica gel and recrystallized from diethyl ether to yield 5-phenyltetrazolo[1,5-a][1,2,4]triazolo[1,5-c]pyrimidine-6-ethanol, acetate (ester) having the structural formula ##STR23## and the azido tautomer thereof as a white solid having a melting point of 114° C. and the following elemental analysis:

Workup

  1. customis evaporated to dryness
  2. customyielding a crude product
  3. customThe crude product is chromatographed on silica gel
  4. customrecrystallized from diethyl ether

Sources & evidence

ORD record
ord-faa57949f5054615903255d8e1f89991
Source dataset
uspto-grants-1985_12
Patent number
US04562192

Reaction notes

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