Sulfuric Acid → 4-Tert-Butylaniline

HRID 1723456Notes

Reaction equation

HRID 1723456 reaction equation
C(Cl)(Cl)(Cl)Cl.S(=O)(=O)(O)O.C(Cl)(Cl)=O.C1(C)C=CC=CC=1.[C:22]([C:26]1[CH:32]=[CH:31][C:29]([NH2:30])=[CH:28][CH:27]=1)([CH3:25])([CH3:24])[CH3:23]>C1(C)C=CC=CC=1>[C:22]([C:26]1[CH:27]=[CH:28][C:29]([NH2:30])=[CH:31][CH:32]=1)([CH3:25])([CH3:23])[CH3:24]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 5943Carbon TetrachlorideHCID 6371Phosgene2×HCID 20025728HCID 20025728, compound

Product 1

HCID 698614-Tert-Butylaniline

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

While carbon tetrachloride was refluxed, fuming sulfuric acid was added dropwise to evolve phosgene. When the atmosphere in the apparatus was replaced sufficiently with phosgene, a 4-t-butylaniline toluene solution (containing 6.00 g of 4-t-butylaniline in 250 ml of toluene) was added dropwise and the temperature was gradually elevated to allow the reaction to proceed while the toluene was refluxed. Yield: 5.61 g (79.6%).

Workup

  1. additionwas added dropwise
  2. customthe reaction
  3. temperaturewas refluxed

Sources & evidence

ORD record
ord-f8fe677c84dd444cacc89715c0d6b6b0
Source dataset
uspto-grants-1989_08
Patent number
US04861872

Reaction notes

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