Hydrochloric Acid → N-ethyl-4-azido-3-benzyloxybenzamide

HRID 1717358Notes

Reaction equation

HRID 1717358 reaction equation
[CH2:1]([NH:3][C:4](=[O:20])[C:5]1[CH:10]=[CH:9][C:8]([NH2:11])=[C:7]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:6]=1)[CH3:2].Cl.N([O-])=O.[Na+].[N-:26]=[N+:27]=[N-].[Na+]>O.C(O)(=O)C.C(OCC)(=O)C.CCCCCC>[CH2:1]([NH:3][C:4](=[O:20])[C:5]1[CH:10]=[CH:9][C:8]([N:11]=[N+:26]=[N-:27])=[C:7]([O:12][CH2:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:6]=1)[CH3:2]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 33557Sodium AzideHCID 23668193Sodium NitriteHCID 586373794-amino-3-(benzyloxy)-N-ethylbenzamide

Product 1

HCID 86629808N-ethyl-4-azido-3-benzyloxybenzamideYield 79.3%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

N-Ethyl-4-amino-3-benzyloxybenzamide (900 mg, 3.33 mmol) obtained in Example 312c) was dissolved in water (9 ml) and acetic acid (6 ml), 1N hydrochloric acid (3.33 ml, 1.0 eq.) was added. An aqueous solution (3 ml) of sodium nitrite (234 mg, 3.33 mmol, 1.0 eq.) was added at 0° C., and the mixture was stirred for 20 min. An aqueous solution (3 ml) of sodium azide (221 mg, 3.33 mmol, 1.0 eq.) was further added, and the mixture was stirred at 0° C. for 1.5 hr. The reaction mixture was diluted with ethyl acetate-hexane (3:1, 50 ml), washed sequentially with water, 0.1N hydrochloric acid, saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous sodium sulfate and concentrated, and diethyl ether was added to the residue. The precipitate was collected by filtration, washed with diethyl ether and dried to give the title compound as a yellow powder (782 mg, 2.64 mmol, 79.2%).

Workup

  1. stirringthe mixture was stirred at 0° C. for 1.5 hr
  2. washwashed sequentially with water, 0.1N hydrochloric acid, saturated aqueous sodium hydrogen carbonate solution and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. additiondiethyl ether was added to the residue
  6. filtrationThe precipitate was collected by filtration
  7. washwashed with diethyl ether
  8. customdried

Sources & evidence

ORD record
ord-bf59625d5adc4fe582a8a968ffb4cb37
Source dataset
uspto-grants-2010_09
Patent number
US07803822B2

Reaction notes

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