Hydrochloric Acid → HCID 86603004, compound

HRID 735417Notes

Reaction equation

HRID 735417 reaction equation
[NH2:1][C:2]1[C:10]([C:11]([F:14])([F:13])[F:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].Cl.N([O-])=O.[Na+].CC([O-])=O.[Na+].[N-:25]=[N+:26]=[N-].[Na+]>O>[N:1]([C:2]1[C:10]([C:11]([F:12])([F:13])[F:14])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5])=[N+:25]=[N-:26]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 33557Sodium AzideHCID 517045Sodium AcetateHCID 6045692-Amino-3-(trifluoromethyl)benzoic acidHCID 23668193Sodium Nitrite

Product 1

HCID 86603004HCID 86603004, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
5 °C

Procedure

A mixture of 1.67 g (10 mmol) of 2-amino-3-(trifluoromethyl)-benzoic acid (compound of formula (VIII)) with 40 ml of 6N HCl was cooled down to 5° C. and a solution of 760 mg of NaNO2 (11 mmol) in 17 ml of water were added dropwise in such a way that the temperature of the reaction mixture did not exceed 7° C. The resulting solution was stirred at this temperature for 30 minutes and then added slowly to a solution of 20.5 g of NaOAc and 715 mg (11 mmol) of NaN3 in 40 ml of water. The reaction mixture was stirred overnight at room temperature. The product was extracted with CH2Cl2 three times. The solvent was removed in vacuo and the residue dried in a desiccator over P2O5 affording the required compound in quantitative yleld.

Workup

  1. customdid not exceed 7° C
  2. stirringThe reaction mixture was stirred overnight at room temperature
  3. extractionThe product was extracted with CH2Cl2 three times
  4. customThe solvent was removed in vacuo
  5. dry with materialthe residue dried in a desiccator over P2O5 affording the required compound in quantitative yleld

Sources & evidence

ORD record
ord-4a765640805449529c627d6033a5bf0f
Source dataset
uspto-grants-2009_09
Patent number
US07592363B2

Reaction notes

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