1,2-Dichloroethane → HCID 797770, compound

HRID 1945382Notes

Reaction equation

HRID 1945382 reaction equation
[N+:1]([C:4]1[CH:14]=[CH:13][C:7]([O:8][CH2:9][C:10]([OH:12])=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH3:15][O:16][C:17](=[O:25])[C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([NH2:24])[CH:19]=1.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.C(Cl)CCl>CN(C=O)C>[CH3:15][O:16][C:17](=[O:25])[C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([NH:24][C:10](=[O:12])[CH2:9][O:8][C:7]2[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:14][CH:13]=2)[CH:19]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 15720(4-Nitrophenoxy)acetic acidHCID 757711-HydroxybenzotriazoleHCID 78274Benzoic acid, 3-amino-, methyl esterHCID 81531Diisopropylethylamine

Product 1

HCID 797770HCID 797770, compoundYield 90.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of the 4-nitrophenoxy acetic acid (100 mg, 0.5 mmol), 3-amino benzoic acid methyl ester (115 mg, 0.76 mmol), HOBt (102.81 mg, 0.76 mmol) and DIPEA (98.34 mg, 0.76 mmol) in DMF (4.0 mL) were added EDC (145.86 mg, 0.76 mmol) at room temperature. After reaction terminated, the reaction mixture in cool water was diluted with Ethyl acetate. The organic phase was washed with aqueous sodium bicarbonate and dried (anhydrous MgSO4), and concentrated. Purification by silica gel column chromatography (Ethyl acetate:Hexane=1:9˜1:1) gave 3-[2-(4-nitro-phenoxy)acetyl-amino]-benzoic acid methyl ester as a white solid (150 mg, 89% yield).

Workup

  1. customAfter reaction
  2. customterminated
  3. additionthe reaction mixture in cool water was diluted with Ethyl acetate
  4. washThe organic phase was washed with aqueous sodium bicarbonate
  5. dry with materialdried (anhydrous MgSO4)
  6. concentrationconcentrated
  7. customPurification by silica gel column chromatography (Ethyl acetate:Hexane=1:9˜1:1)

Sources & evidence

ORD record
ord-a895fcc91a254a9f971245af41382fbd
Source dataset
uspto-grants-2013_03
Patent number
US08394799B2

Reaction notes

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