Aniline → 3-Nitrobenzanilide

HRID 610074

Reaction equation

HRID 610074 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[N+:15]([C:18]1[CH:19]=[C:20]([CH:24]=[CH:25][CH:26]=1)[C:21](Cl)=[O:22])([O-:17])=[O:16].C(=O)(O)[O-].[Na+]>ClCCl>[N+:15]([C:18]1[CH:19]=[C:20]([CH:24]=[CH:25][CH:26]=1)[C:21]([NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:22])([O-:17])=[O:16]

Participants

6

Reactant 4

HCID 6115AnilineHCID 8471TriethylamineHCID 8495Benzoyl chloride, 3-nitro-HCID 516892Sodium Bicarbonate

Product 1

HCID 3477553-Nitrobenzanilide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a cooled (0° C.) solution of aniline (17 g, 180 mmol) and triethylamine (27 mL, 190 mmol) in dichloromethane (100 mL) was added a solution of 3-nitrobenzoyl chloride (30 g, 160 mmol) in dichloromethane (60 mL). The mixture was stirred for 15 min at 0° C. then overnight at room temperature. It was then poured into saturated sodium bicarbonate (1 L) and stirred vigorously for 15 min. The precipitate was collected, washed with water and dried (40 g, 100%).

Workup

  1. customovernight
  2. customat room temperature
  3. stirringstirred vigorously for 15 min
  4. customThe precipitate was collected
  5. washwashed with water
  6. customdried (40 g, 100%)

Sources & evidence

ORD record
ord-68e152fdc1f3477bba21a2bec2bf8b0b
Source dataset
uspto-grants-1999_12
Patent number
US05998463

Linked notes

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