4-Chloroaniline → 1-(4-Chlorophenyl)-3-(3-(2-methyl-1,3-dioxolan-2-yl)benzyl)urea

HRID 64229Notes

Reaction equation

HRID 64229 reaction equation
[CH3:1][C:2]1([C:7]2[CH:8]=[C:9]([CH:24]=[CH:25][CH:26]=2)[CH2:10][NH:11][C:12](=[O:23])OC2C=CC([N+]([O-])=O)=CC=2)[O:6][CH2:5][CH2:4][O:3]1.[Cl:27][C:28]1[CH:34]=[CH:33][C:31]([NH2:32])=[CH:30][CH:29]=1.C(N(CC)CC)C>ClCCl>[Cl:27][C:28]1[CH:34]=[CH:33][C:31]([NH:32][C:12]([NH:11][CH2:10][C:9]2[CH:24]=[CH:25][CH:26]=[C:7]([C:2]3([CH3:1])[O:3][CH2:4][CH2:5][O:6]3)[CH:8]=2)=[O:23])=[CH:30][CH:29]=1

Participants

5

Reactant 3

HCID 78124-ChloroanilineHCID 8471TriethylamineHCID 715005354-Nitrophenyl 3-(2-methyl-1,3-dioxolan-2-yl)benzylcarbamate

Product 1

HCID 715005361-(4-Chlorophenyl)-3-(3-(2-methyl-1,3-dioxolan-2-yl)benzyl)ureaYield 71%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Nitrophenyl-N-benzylcarbamate 21 (267 mg, 0.767 mmol) was added to a solution of 4-chloroaniline (97 mg, 0.767 mmol) and triethylamine in dichloromethane (5 mL). The mixture was stirred at room temperature until starting materials were consumed. The reaction mixture was then diluted with dichloromethane (50 mL) and washed with aq. NaOH, water and brine. The organic layer was dried over anhydrous MgSO4, filtered and concentrated The residue was purified by column chromatography eluting with methanol/chloroform to give 22 (165 mg, 71%). 1H NMR (CDCl3, 400 MHz) δ 1.58 (s, 3H), 3.71 (t, J=6.8 Hz, 2H), 3.99 (t, J=6.8 Hz, 2H), 4.36 (d, J=5.6 Hz, 2H), 6.78 (s, 1H), 7.16-7.18 (m, 4H), 7.23-7.26 (m, 1H), 7.35 (d, J=5.6 Hz, 2H).

Workup

  1. customwere consumed
  2. additionThe reaction mixture was then diluted with dichloromethane (50 mL)
  3. washwashed with aq. NaOH, water and brine
  4. dry with materialThe organic layer was dried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated The residue
  7. customwas purified by column chromatography
  8. washeluting with methanol/chloroform

Sources & evidence

ORD record
ord-4663fb4141974a2587606b65746737a8
Source dataset
uspto-grants-2016_09
Patent number
US09447134B2

Reaction notes

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