1,2-Dichloroethane → HCID 15885812, compound

HRID 1840868Notes

Reaction equation

HRID 1840868 reaction equation
[CH2:1]([NH:3][C:4](=[O:16])[NH:5][C:6]1[CH:14]=[CH:13][CH:12]=[C:11]([CH3:15])[C:7]=1[C:8]([OH:10])=O)[CH3:2].C(N(CC)CC)C.C(Cl)CCl>C(Cl)Cl.CCOC(C)=O>[CH2:1]([NH:3][C:4]1[O:16][C:8](=[O:10])[C:7]2[C:11]([CH3:15])=[CH:12][CH:13]=[CH:14][C:6]=2[N:5]=1)[CH3:2]

Participants

6

Reactant 3

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 15885811HCID 15885811, compound

Product 1

HCID 15885812HCID 15885812, compoundYield 55.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 2-(3-ethylureido)-6-methylbenzoic acid (250 mg, 1.125 mmol) and triethylamine (170 mg, 1.69 mmol) in 10 mL CH2Cl2 at room temperature was added EDC (501 mg, 1.69 mmol). After stirring at room temperature for 3 hours, the reaction mixture was diluted with EtOAc and washed sequentially with 1N HCl and sat'd. NaHCO3. The organic fraction was dried (MgSO4), filtered and evaporated under reduced pressure. Silica gel chromatography of the residue (1:1 EtOAc/hexane) afforded 127 mg of product: Anal. Calc'd. for C11H12N2O2.0.25H2O: C, 63.30; H, 6.04; N, 13.42. Found: C, 63.32; H, 5.92; N, 13.10. 1H-NMR (300 MHz, d6-DMSO) δ 1.14 (t, J=7 Hz, 3H), 2.60 (s, 3H), 3.27 (pent, J=7 Hz, 2H), 6.95 (d, J=8 Hz, 1H), 7.02 (d, J=8 Hz, 1H), 7.50 (t, J=8 Hz, 1H), 7.90 (br. t, J=7 Hz, 1H, exchangeable).

Workup

  1. washwashed sequentially with 1N HCl
  2. dry with materialThe organic fraction was dried (MgSO4)
  3. filtrationfiltered
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-0709f946d6e04968868385451de9fb6a
Source dataset
uspto-grants-2004_01
Patent number
US06683077B2

Reaction notes

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