Hydrochloric Acid → HCID 53904716, compound

HRID 1274191Notes

Reaction equation

HRID 1274191 reaction equation
N([O-])=O.[Na+].[NH2:5][C:6]1[CH:7]=[C:8]([CH:13]=[CH:14][C:15]=1[C@H:16]([NH:18][C:19](=[O:21])[CH3:20])[CH3:17])[C:9]([O:11][CH3:12])=[O:10].Cl.[N-:23]=[N+:24]=[N-].[Na+]>O>[C:19]([NH:18][C@@H:16]([C:15]1[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][C:6]=1[N:5]=[N+:23]=[N-:24])[CH3:17])(=[O:21])[CH3:20]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 33557Sodium AzideHCID 12109152HCID 12109152, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 53904716HCID 53904716, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Sodium nitrite (440 mg) was added to a mixture of methyl (R)-3-amino-4-(1-acetylaminoethyl)benzoate (1.38 g), conc. hydrochloric acid (3 ml) and water (9 ml) under ice-cooling, and the mixture was stirred at the same temperature for 30 minutes. A solution of sodium azide (420 mg) in water (5 ml) was added, and the mixture was stirred for 30 minutes. After the reaction, the mixture was extracted with ethyl acetate, and washed with water. The mixture was dried, and the solvent was evaporated to give methyl (R)-4-(1-acetylaminoethyl)-3-azidobenzoate as white crystals.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred for 30 minutes
  3. customAfter the reaction
  4. extractionthe mixture was extracted with ethyl acetate
  5. washwashed with water
  6. customThe mixture was dried
  7. customthe solvent was evaporated

Sources & evidence

ORD record
ord-71df643eed734f5ab0951cd86876d001
Source dataset
uspto-grants-2000_12
Patent number
US06156766

Reaction notes

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