4-Tert-Butylaniline → HCID 44452554, compound

HRID 711305Notes

Reaction equation

HRID 711305 reaction equation
[C:1]([C:5]1[CH:11]=[CH:10][C:8]([NH2:9])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[Cl:12][CH2:13][CH2:14][CH2:15][N:16]=[C:17]=[O:18]>C1(C)C=CC=CC=1>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([NH:9][C:17]([NH:16][CH2:15][CH2:14][CH2:13][Cl:12])=[O:18])=[CH:10][CH:11]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 698614-Tert-ButylanilineHCID 166752Propane, 1-chloro-3-isocyanato-

Product 1

HCID 44452554HCID 44452554, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 4-tert-butylaniline (1.0 g, 1.07 mmol) in 5 mL toluene was added 3-chloropropylisocyanate (0.69 mL, 6.70 mmol). The reaction was allowed to stir at ambient temperature for 16 h. The reaction was partitioned between saturated NaHCO3 and ethylacetate. The organics were washed with water and brine, then dried over Na2SO4, filtered and concentrated. The residue was purified by silica gel chromatography to give 1-(4-tert-butylphenyl)-3-(3-chloropropyl)urea (31%). LCMS [M+H]+=269.2.

Workup

  1. customThe reaction was partitioned between saturated NaHCO3 and ethylacetate
  2. washThe organics were washed with water and brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-7e824aa528d9484baa8b2128fb45e26b
Source dataset
uspto-grants-2015_11
Patent number
US09181261B2

Reaction notes

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