Ammonia → HCID 19348480, compound

HRID 1751852Notes

Reaction equation

HRID 1751852 reaction equation
[C:1]([C:5]1[CH:13]=[CH:12][C:8]([C:9](O)=[O:10])=[CH:7][C:6]=1[N+:14]([O-:16])=[O:15])([CH3:4])([CH3:3])[CH3:2].OC1C2N=N[NH:23]C=2C=CC=1.C1(N=C=NC2CCCCC2)CCCCC1.N.CC(O)C.C([O-])(O)=O.[Na+]>ClCCl>[C:1]([C:5]1[CH:13]=[CH:12][C:8]([C:9]([NH2:23])=[O:10])=[CH:7][C:6]=1[N+:14]([O-:16])=[O:15])([CH3:4])([CH3:3])[CH3:2]

Participants

8

Reactant 6

HCID 222AmmoniaHCID 3776IsopropanolHCID 10868DicyclohexylcarbodiimideHCID 516892Sodium BicarbonateHCID 7388134-Tert-butyl-3-nitrobenzoic acidHCID 178418300HCID 178418300, compound

Product 1

HCID 19348480HCID 19348480, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-tert-butyl-3-nitrobenzoic acid (0.1 mole), hydroxybenzotriazole (HOBt, 0.12 mole) and dicyclohexylcarbodiimide (DCC, 0.11 mole) in dichloromethane (100 mL) is stirred at room temperature while a solution of ammonia in 2-propanol (2.0M, 75 mL, 0.12 mole) is added rapidly. The mixture is stirred for two hours at room temperature, and poured into aqueous NaHCO3 (5%, 200 mL). The layers are separated, and the aqueous phase is extracted with dichloromethane (2×200 mL). The combined organics are washed (2×200 mL 5% aq. NaHCO3), dried (sat'd aq. NaCl, Na2SO4), filtered and concentrated. The product is recrystallized from EtOH-water to afford pure 4-tert-butyl-3-nitrobenzamide.

Workup

  1. additionis added rapidly
  2. customThe layers are separated
  3. extractionthe aqueous phase is extracted with dichloromethane (2×200 mL)
  4. washThe combined organics are washed (2×200 mL 5% aq. NaHCO3)
  5. dry with materialdried (sat'd aq. NaCl, Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe product is recrystallized from EtOH-water

Sources & evidence

ORD record
ord-b579243f972842d19541dec8757c0ae1
Source dataset
uspto-grants-2015_10
Patent number
US09161997B2

Reaction notes

Loading…