Dimethyl Sulfoxide → HCID 86699138, compound

HRID 1424237Notes

Reaction equation

HRID 1424237 reaction equation
CS(C)=O.[C:5]([C:9]1[CH:14]=[CH:13][C:12]([NH2:15])=[C:11]([N+:16]([O-:18])=[O:17])[CH:10]=1)([CH3:8])([CH3:7])[CH3:6].[OH-].[K+].[CH2:21](Br)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>O.C1(C)C=CC=CC=1>[CH2:21]([NH:15][C:12]1[CH:13]=[CH:14][C:9]([C:5]([CH3:8])([CH3:6])[CH3:7])=[CH:10][C:11]=1[N+:16]([O-:18])=[O:17])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 7498Benzyl BromideHCID 14797Potassium HydroxideHCID 805734-tert-Butyl-2-nitroaniline

Product 1

HCID 86699138HCID 86699138, compoundYield 63.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A reactor was charged with DMSO (6 L), followed by 4-tert-butyl-2-nitrophenylamine (Preparation 108, 3.0 kg, 15.4 mol) and potassium hydroxide (1.32 kg, 23.5 mol). The mixture was stirred at room temperature for twenty minutes. Toluene (12 L) was added and the mixture stirred for another twenty minutes. After cooling to 10° C., benzyl bromide (3.16 kg, 18.5 mol) was added slowly and the reaction mixture was stirred for 4 hours. Water (30 L) was added, the mixture stirred for 30 minutes and the layers allowed to settle. The aqueous layer was extracted with toluene (2×10 L), followed by ethyl acetate (10 L), and the combined organic extracts concentrated under vacuum at <50° C. Isopropanol (4 L) was added and the mixture cooled to −5° C. The slurry was stirred for 1 hour before collecting the solids by filtration, washing with isopropanol (2×1.5 L) and drying at 55-60° C. to provide 2.8 kg of the title compound.

Workup

  1. stirringthe mixture stirred for another twenty minutes
  2. temperatureAfter cooling to 10° C.
  3. stirringthe reaction mixture was stirred for 4 hours
  4. stirringthe mixture stirred for 30 minutes
  5. extractionThe aqueous layer was extracted with toluene (2×10 L)
  6. concentrationthe combined organic extracts concentrated under vacuum at <50° C
  7. additionIsopropanol (4 L) was added
  8. temperaturethe mixture cooled to −5° C
  9. stirringThe slurry was stirred for 1 hour
  10. custombefore collecting the solids
  11. filtrationby filtration
  12. washwashing with isopropanol (2×1.5 L)
  13. customdrying at 55-60° C.

Sources & evidence

ORD record
ord-48de0d714681464e8d94631719b683c0
Source dataset
uspto-grants-2015_01
Patent number
US08927587B2

Reaction notes

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