Hydrochloric Acid → HCID 18506136, compound

HRID 1357390Notes

Reaction equation

HRID 1357390 reaction equation
[CH2:1]([N:8]1[C:12]([C:13]2[CH:14]=[C:15]([CH:27]=[CH:28][C:29]=2[C:30]2[N:34]([CH2:35][C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[N:33]=[N:32][N:31]=2)[O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[NH:23]C(=O)C)=[N:11][N:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>C(O)C>[CH2:1]([N:8]1[C:12]([C:13]2[CH:14]=[C:15]([CH:27]=[CH:28][C:29]=2[C:30]2[N:34]([CH2:35][C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[N:33]=[N:32][N:31]=2)[O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[NH2:23])=[N:11][N:10]=[N:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 18506085HCID 18506085, compound

Product 1

HCID 18506136HCID 18506136, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

N-{2-[3,4-Bis-(1-benzyl-1H-tetrazol-5-yl)phenoxy]phenyl}acetamide (40 mg, 0.07 mmol) was dissolved in ethanol (10 ml). 4N hydrochloric acid (10 ml) was added and the reaction mixture was refluxed for 15 hours. The mixture was evaporated in vacuo and redissolved in methylene chloride and 0.5 N aqueous sodium hydroxide (1:1) (20 ml). The organic phase was dried over magnesium sulphate and evaporated in vacuo to give 2-[3,4-bis-(1-benzyl-1H-tetrazol-5-yl)phenoxy]phenylamine as an oil (yield: 37 mg (100%)). 1H-NMR (CDCl3 in ppm): 3.9 (2H, broad s); 5.58 (4H, s); 6.75 (1H, d.d.); 6.85 (1H,d.d.); 6.9 (1H,d.d.); 7.0 (1H,d.d.); 7.1 (1H,d.d.); 7.2-7.4 (10H,m); 7.48 (1H,d); 7.8 (1H,d).

Workup

  1. temperaturethe reaction mixture was refluxed for 15 hours
  2. customThe mixture was evaporated in vacuo
  3. dissolutionredissolved in methylene chloride
  4. dry with materialThe organic phase was dried over magnesium sulphate
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-378b6325aba744d4b0b27aee85339c52
Source dataset
uspto-grants-2003_07
Patent number
US06590118B1

Reaction notes

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