Ethyl 6-isocyanatohexanoate → 6-[3-(4-Bromo-3-methyl-5-nitro-phenyl)-ureido]-hexanoic acid ethyl ester

HRID 723215Notes

Reaction equation

HRID 723215 reaction equation
[CH2:1]([O:3][C:4](=[O:13])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][N:10]=[C:11]=[O:12])[CH3:2].[Br:14][C:15]1[C:20]([N+:21]([O-:23])=[O:22])=[CH:19][C:18]([NH2:24])=[CH:17][C:16]=1[CH3:25]>C(Cl)Cl.CCOC(C)=O>[CH2:1]([O:3][C:4](=[O:13])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][NH:10][C:11]([NH:24][C:18]1[CH:19]=[C:20]([N+:21]([O-:23])=[O:22])[C:15]([Br:14])=[C:16]([CH3:25])[CH:17]=1)=[O:12])[CH3:2]

Participants

5

Reactant 2

HCID 3445675Ethyl 6-isocyanatohexanoateHCID 218864724-Bromo-3-methyl-5-nitroaniline

Product 1

HCID 695868146-[3-(4-Bromo-3-methyl-5-nitro-phenyl)-ureido]-hexanoic acid ethyl esterYield 36%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

6-Isocyanato-hexanoic acid ethyl ester (370 μL, 2.16 mmol) was added to a solution of 4-bromo-3-methyl-5-nitro-phenylamine (250 mg, 1.08 mmol, Example 135: step a) in CH2Cl2 (5 mL, anhydrous) at rt. The reaction mixture was stirred overnight, then diluted in EtOAc and washed with saturated NH4Cl solution, water, and brine. The organic layer was dried over magnesium sulfate. Removal of solvents in vacuo was followed by flash chromatography (50–75% EtOAc/hexanes) to afford the title compound as a brown oil (162 mg, 36%). 1H-NMR (CDCl3): δ 7.59 (d, 1H, J=2.56 Hz), 7.42–7.48 (m, 1H), 4.10–4.17 (m, 2H), 3.20–3.28 (m, 2H), 2.39 (s, 3H), 2.29–2.35 (m, 2H), 1.47–1.68 (m, 4H), 1.23–1.41 (m, 5H).

Workup

  1. customat rt
  2. washwashed with saturated NH4Cl solution, water, and brine
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. customRemoval of solvents in vacuo

Sources & evidence

ORD record
ord-7bd146f7cb64447fbac0d743ba700855
Source dataset
uspto-grants-2006_11
Patent number
US07138530B2

Reaction notes

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