1-Tert-butyl-4-isocyanatobenzene → N-[3-chloro-4-(isopropylsulfonyl)thien-2-yl]-N'-(4-t-butyl-phenyl)urea

HRID 965126Notes

Reaction equation

HRID 965126 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([S:8]([CH:11]([CH3:13])[CH3:12])(=[O:10])=[O:9])[C:6]=1[Cl:7].[C:14]([C:18]1[CH:23]=[CH:22][C:21]([N:24]=[C:25]=[O:26])=[CH:20][CH:19]=1)([CH3:17])([CH3:16])[CH3:15]>N1C=CC=CC=1>[Cl:7][C:6]1[C:5]([S:8]([CH:11]([CH3:13])[CH3:12])(=[O:10])=[O:9])=[CH:4][S:3][C:2]=1[NH:1][C:25]([NH:24][C:21]1[CH:22]=[CH:23][C:18]([C:14]([CH3:17])([CH3:16])[CH3:15])=[CH:19][CH:20]=1)=[O:26]

Participants

4

Reactant 2

HCID 27356951-Tert-butyl-4-isocyanatobenzeneHCID 190755712-Amino-3-chloro-4-isopropylsulfonylthiophene

Product 1

HCID 19075580N-[3-chloro-4-(isopropylsulfonyl)thien-2-yl]-N'-(4-t-butyl-phenyl)ureaYield 35.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2-Amino-3-chloro-4-isopropylsulfonylthiophene (260 mg) was stirred for 4 hours with 4-t-butylphenylisocyanate (119 mg) in 1 mL of pyridine at 60 ∞C. The pyridine was evaporated to dryness and the residue taken up in a mixture of ethyl acetate and 1N hydrochloric acid. The ethyl acetate layer was washed with water, saturated sodium bicarbonate and brine, and dried over anhydrous magnesium sulfate. Concentration and crystallization of the residue from ethanol and water gave 100 mg of N-[3-chloro-4-(isopropylsulfonyl)thien-2-yl]-N'-(4-t-butyl-phenyl)urea, an off-white solid.

Workup

  1. customThe pyridine was evaporated to dryness
  2. additionthe residue taken up in a mixture of ethyl acetate and 1N hydrochloric acid
  3. washThe ethyl acetate layer was washed with water, saturated sodium bicarbonate and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationConcentration and crystallization of the residue from ethanol and water

Sources & evidence

ORD record
ord-7028070b73ce43888eeb677a847b450a
Source dataset
uspto-grants-1998_06
Patent number
US05773459

Reaction notes

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