Toluene → HCID 21460761, compound

HRID 1488807Notes

Reaction equation

HRID 1488807 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 1140Toluene2×HCID 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 vacuo and reconcentrate two more 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 temperture. 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 vacuo
  4. customthe reaction at room temperture
  5. concentrationConcentrate
  6. customthe reaction in vacuo

Sources & evidence

ORD record
ord-b2b906d74abe40f3b8f5f4eb253d9752
Source dataset
uspto-grants-1997_10
Patent number
US05675018

Reaction notes

Loading…