Toluene → HCID 21460761, compound

HRID 2396332Notes

Reaction equation

HRID 2396332 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[C:4]([N+:11]([O-:13])=[O:12])[CH:3]=1.S(Cl)(Cl)=O.C([NH2:22])(C)(C)C.[C:23]1([CH3:29])[CH:28]=CC=C[CH:24]=1>C(Cl)Cl>[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:22])=[O:8])=[C:4]([N+:11]([O-:13])=[O:12])[C:3]=1[C:23]([CH3:29])([CH3:28])[CH3:24]

Participants

6

Reactant 4

HCID 1140TolueneHCID 6385Tert-ButylamineHCID 24386Thionyl ChlorideHCID 27374164-Fluoro-2-nitrobenzoic acid

Product 1

HCID 21460761HCID 21460761, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

Suspend 4-fluoro-2-nitro-benzoic acid (4.5 g, 24.3 mmol) in toluene (20 mL), add thionyl chloride (22.5 mL) seal the flask and warm to 50° C. for 3 hours. Concentrate the reaction in in vacuo and reconcentrate twomore times from toluene. Place under high vacuum for 1 hour. Dissolve the acid chloride in methylene chloride (40 mL) and add t-butylamine (13.5 mL). Stir the reaction at room temperature. Concentrate the reaction in vacuo to yield the 4-fluoro-2-nitro-tert-butylbenzamide as an off white solid (5.5 g, 95%); mp 142°-143° C.

Workup

  1. customseal the flask
  2. concentrationConcentrate
  3. customthe reaction in in vacuo and reconcentrate twomore times from toluene
  4. customthe reaction at room temperature
  5. concentrationConcentrate
  6. customthe reaction in vacuo

Sources & evidence

ORD record
ord-0e90d73cefbd46fcb90284082c35fcb1
Source dataset
uspto-grants-1996_02
Patent number
US05491153

Reaction notes

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