Aniline → HCID 86603005, compound

HRID 735418Notes

Reaction equation

HRID 735418 reaction equation
[N:1]([C:4]1[C:12]([C:13]([F:16])([F:15])[F:14])=[CH:11][CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=O)=[N+:2]=[N-:3].[NH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C([O-])(O)=O.[Na+]>O=S(Cl)Cl>[N:1]([C:4]1[C:12]([C:13]([F:16])([F:15])[F:14])=[CH:11][CH:10]=[CH:9][C:5]=1[C:6]([NH:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:8])=[N+:2]=[N-:3]

Participants

5

Reactant 3

HCID 6115AnilineHCID 516892Sodium BicarbonateHCID 86603004HCID 86603004, compound2×

Product 1

HCID 86603005HCID 86603005, compound

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent

Conditions

Temperature
80 °C

Procedure

2-Azido-3-trifluoromethyl-benzoic acid (460 mg, 2 mmol, compound IX) was dissolved in 2 ml of SOCl2 and the reaction mixture was heated at 80° C. for 1 hour. The remaining SOCl2 was evaporated in vacuo and the residue was coevaporated with dry benzene. Dry CH2Cl2 (2 ml) was added followed by a dropwise addition of 200 μl of aniline (2 mmol). The reaction mixture was stirred at room temperature for 1 hour. Saturated aq. NaHCO3 was added and the product was extracted with CH2Cl2. The resulting amide was purified by recrystallization from methanol. The yleld was 521 mg (86%).

Workup

  1. customThe remaining SOCl2 was evaporated in vacuo
  2. additionDry CH2Cl2 (2 ml) was added
  3. extractionthe product was extracted with CH2Cl2
  4. customThe resulting amide was purified by recrystallization from methanol

Sources & evidence

ORD record
ord-428ea428d7704fe5845e122870cbf3c2
Source dataset
uspto-grants-2009_09
Patent number
US07592363B2

Reaction notes

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