Hydrochloric Acid → HCID 12798026, compound

HRID 1106022Notes

Reaction equation

HRID 1106022 reaction equation
Cl.[NH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([CH:20]([CH3:22])[CH3:21])[C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:11])=[CH:5][CH:4]=1.N([O-])=O.[Na+].[N-:27]=[N+:28]=[N-].[Na+]>C(O)(=O)C.O>[N:2]([C:3]1[CH:4]=[CH:5][C:6]([CH:9]([CH:20]([CH3:22])[CH3:21])[C:10]([O:12][CH2:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)=[O:11])=[CH:7][CH:8]=1)=[N+:27]=[N-:28]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 33557Sodium AzideHCID 12798025HCID 12798025, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 12798026HCID 12798026, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent4×

Procedure

To a stirred solution of 20 ml of water and 11 ml of concentrated hydrochloric acid at <10° was added a solution of 14.17 g of 2-(4-aminophenyl)-3-methylbutanoic acid, benzyl ester in 50 ml of acetic acid. At 0° to 5° was added a solution of 3.62 g of sodium nitrite in 12.5 ml of water. The mixture was stirred at 0° to 5° for an additional 45 minutes, then poured into a stirred solution of 3.25 g of sodium azide in 12.5 ml of water in an ice-cooled beaker. Gas evolved immediately along with formation of orange oil. After 3-4 minutes, the mixture was diluted with water to 400 ml, then extracted with butyl chloride. The butyl chloride solution was washed with water (3 times) and saturated sodium bicarbonate solution, dried (MgSO4) and evaporated to 13.5 g of oil, 2-(4-azidophenyl)-3-methylbutanoic acid, benzyl ester, which began to solidify. The infrared spectrum of the oil shows absorption peaks at 2130 cm-1 (azide) and 1740 cm-1 (ester carbonyl). Thin-layer chromatography on silica gel-coated plates in chloroform or butyl chloride showed only one spot.

Workup

  1. temperaturecooled beaker
  2. waitAfter 3-4 minutes
  3. extractionextracted with butyl chloride
  4. washThe butyl chloride solution was washed with water (3 times) and saturated sodium bicarbonate solution
  5. dry with materialdried (MgSO4)
  6. customevaporated to 13.5 g of oil, 2-(4-azidophenyl)-3-methylbutanoic acid, benzyl ester, which
  7. customThe infrared spectrum of the oil shows absorption peaks at 2130 cm-1 (azide) and 1740 cm-1 (ester carbonyl)

Sources & evidence

ORD record
ord-02f4a54c01f9479ab120ae0b8b6c5e49
Source dataset
uspto-grants-1982_01
Patent number
US04311696

Reaction notes

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