2,6-Diisopropylphenyl isocyanate → 1-(1-Benzenesulfonylcyclopentylmethyl)-3-(2,6-diisopropyl-phenyl)-urea

HRID 2061641Notes

Reaction equation

HRID 2061641 reaction equation
[N:1]([C:4]1[C:9]([CH:10]([CH3:12])[CH3:11])=[CH:8][CH:7]=[CH:6][C:5]=1[CH:13]([CH3:15])[CH3:14])=[C:2]=[O:3].[C:16]1([S:22]([C:25]2([CH2:30][NH2:31])[CH2:29][CH2:28][CH2:27][CH2:26]2)(=[O:24])=[O:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>ClCCl>[C:16]1([S:22]([C:25]2([CH2:30][NH:31][C:2]([NH:1][C:4]3[C:5]([CH:13]([CH3:15])[CH3:14])=[CH:6][CH:7]=[CH:8][C:9]=3[CH:10]([CH3:11])[CH3:12])=[O:3])[CH2:29][CH2:28][CH2:27][CH2:26]2)(=[O:23])=[O:24])[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

4

Reactant 2

HCID 922592,6-Diisopropylphenyl isocyanateHCID 39871991HCID 39871991, compound

Product 1

HCID 252254811-(1-Benzenesulfonylcyclopentylmethyl)-3-(2,6-diisopropyl-phenyl)-ureaYield 43.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a tube, under nitrogen, 157 mg (0.77 mmol) of 2-isocyanato-1,3-diisopropylbenzene is added to a solution of 168 mg (0.7 mmol) of C-(1-benzenesulfonyl-cyclopentyl)-methylamine in 3.5 ml of dichloromethane. The reaction mixture is stirred at RT for 3 h. The solvent is evaporated with a nitrogen stream. The paste obtained is taken up in heptane (5 mL) for crystallization. The white powder obtained is chromatographed on silica gel (dichloromethane then dichloromethane/methanol, 98/2, v/v). The oil obtained is crystallized from heptane. After filtration and drying, 135 mg of 1-(1-benzenesulfonylcyclopentylmethyl)-3-(2,6-diisopropyl-phenyl)-urea is obtained in the form of a white powder (m.p.=124° C., Yield=44%).

Workup

  1. customThe solvent is evaporated with a nitrogen stream
  2. customThe paste obtained
  3. customis taken up in heptane (5 mL) for crystallization
  4. customThe white powder obtained
  5. customis chromatographed on silica gel (dichloromethane
  6. customThe oil obtained
  7. customis crystallized from heptane
  8. filtrationAfter filtration
  9. customdrying

Sources & evidence

ORD record
ord-ab8873e8ca054dc393af7a5422ca4f5a
Source dataset
uspto-grants-2012_10
Patent number
US08283378B2

Reaction notes

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