1,2-Dichloroethane → Benzoic Acid

HRID 354483Notes

Reaction equation

HRID 354483 reaction equation
COC1C=C(C[C:21]([OH:23])=[O:22])C=CC=1NC(NC1C=CC=CC=1C)=O.[CH:24]1[CH:25]=[CH:26][C:27]2N(O)N=N[C:28]=2[CH:29]=1.C(Cl)CCl.Cl>CN(C1C=CN=CC=1)C.CN(C=O)C>[C:21]([OH:23])(=[O:22])[C:28]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:29]=1

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 313Hydrochloric AcidHCID 757711-HydroxybenzotriazoleHCID 114498403-Methoxy-4-o-tolylureidophenylacetic acid

Product 1

HCID 243Benzoic Acid

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

To a stirred mixture of ethyl 4-(2-allylaminoethoxy)-3-methoxy benzoate (578 mg, 2.1 mmol), 3-methoxy-4-[N′-(2-methylphenyl)ureido]phenylaceticacid (650 mg, 2.1 mmol), HOBt (420 mg, 3.11 mmol), and DMAP (catalytic amount) in DMF (4 mL) was added EDC (596 mg, 3.11 mmol) at room temp. The resulting mixture was stirred for a further 18 hr at room temp. The mixture was poured into 1N HCl and extracted with EtOAc. The extract was washed with brine, dried over Na2SO4, and evaporated in vacuo. The residue was chromatographed on silica-gel with CHCl3:EtOAc (95:5 to 1:1, v/v) as eluent to give 1 g (84%) 3-methoxy-4-[[2-3-methoxy-4-[N′-(2-methylphenyl)ureido]phenylacetyl]allylamino]ethoxy]benzoic acid as a pale-yellow gum. 1H-NMR (CDCl3, 400 MHz) δ1.39 (t, 3H, J=7.3 Hz), 2.29 (s, 3H), 3.58 and 3.63 (s, total 3H), 3.70-3.77 (m, 2H), 3.83 and 3.87 (s, 3H), 4.054.13 (m, 2H), 4.25 (m, 1H), 4.36 (q, 1H, J=7.0 Hz), 5.04-5.22 (m, 2H), 5.73 (m, 1H), 6.32 and 6.47 (s, 1H), 6.69-6.85 (m, 2H, 7.12 (m, 2H), 7.23 (m, 2H), 7.50-7.65 (m, 2H), 8.05 (d, 1H, J=7.8 Hz); MS (FAB) m/z 576(M+H)30.

Workup

  1. extractionextracted with EtOAc
  2. washThe extract was washed with brine
  3. dry with materialdried over Na2SO4
  4. customevaporated in vacuo
  5. customThe residue was chromatographed on silica-gel with CHCl3:EtOAc (95:5 to 1:1

Sources & evidence

ORD record
ord-932d5d22415c4c75911f701215882b04
Source dataset
uspto-grants-2004_06
Patent number
US06756378B2

Reaction notes

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