Sulfuric Acid → HCID 178448759, compound

HRID 2288797Notes

Reaction equation

HRID 2288797 reaction equation
[CH2:1]([N:5]1[C:9]([CH2:10][C:11]2[CH:12]=[CH:13][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[C:23]3[NH:27][N:26]=[N:25][N:24]=3)=[N:15][CH:16]=2)=[N:8][C:7]([CH:28](OC)[O:29]C)=[N:6]1)[CH2:2][CH2:3][CH3:4].S(=O)(=O)(O)O>CC(C)=O>[CH2:1]([N:5]1[C:9]([CH2:10][C:11]2[CH:12]=[CH:13][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[C:23]3[NH:27][N:26]=[N:25][N:24]=3)=[N:15][CH:16]=2)=[N:8][C:7]([CH:28]=[O:29])=[N:6]1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 178448758HCID 178448758, compound

Product 1

HCID 178448759HCID 178448759, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

The compound of Example 26 was treated with catalytic sulfuric acid in wet acetone at reflux. Purification gave 5-[2-[5-[[1-butyl-3-formyl-1H-1,2,4-triazol-5-yl]methyl]-2-pyridinyl)phenyl]-1H-tetrazole as a colorless solid: mp 167-168° C.; NMR (CDCl3) δ 0.94 (t, J=7 Hz, 3H), 1.35 (m, J=7 Hz, 2H), 1.88 (m, J=7 Hz, 2H), 4.22 (t, J=7 Hz, 2H), 4.29 (s, 2H), 7.37 (d, J=8 Hz, 1H), 7.46-7.55 (m, 3H), 7.44 (dd, J=8 and 2 Hz, 1H), 7.93-7.99 (m, 1H), 8.59 (d, J=2 Hz, 1H), 9.95 (s, 1H); MS(FAB) m/e (rel intensity) 389(100), 361(66), 346(26), 333(24), 305(17), 290(23); HRMS. Calc'd. for M+H: 389.1838. Found: 389.1829.

Workup

  1. temperatureat reflux
  2. customPurification

Sources & evidence

ORD record
ord-ee38e8e04f204210bbc972e8c38fd627
Source dataset
uspto-grants-2000_07
Patent number
US06090828

Reaction notes

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