1,2-Dichloroethane → HCID 57857114, compound

HRID 1643312Notes

Reaction equation

HRID 1643312 reaction equation
[CH2:1]([N:8]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:9]1[CH:17]=[CH:16][C:12]([C:13](O)=[O:14])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)CCl.[CH:29]1[CH:30]=[CH:31][C:32]2[N:37](O)N=[N:35][C:33]=2[CH:34]=1.C1(N)C=CC=CC=1N>CN(C=O)C.CCOC(C)=O>[NH2:35][C:33]1[CH:34]=[CH:29][CH:30]=[CH:31][C:32]=1[NH:37][C:13](=[O:14])[C:12]1[CH:11]=[CH:10][C:9]([N:8]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:17][CH:16]=1

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 7243O-PhenylenediamineHCID 757711-HydroxybenzotriazoleHCID 8122187HCID 8122187, compound

Product 1

HCID 57857114HCID 57857114, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-(dibenzylamino)benzoic acid (50 mg, 0.16 mmol) in DMF was added EDC (181 mg, 0.95 mmol), HOBt (128 mg, 0.95 mmol) and phenylenediamine (171 mg, 1.58 mmol) were which was allowed to stir at room temperature for 12 hours. The crude reaction mixture was diluted with EtOAc (20 mL) and then washed with sat.'d aq. NaHCO3 (1×10 mL). The organic layer was dried over MgSO4, filtered, and concentrated in vacuo. The crude residue was purified by reverse-phase chromatography (20-100% MeCN/H2O with 0.05% TFA). The appropriate fractions were combined, diluted with EtOAc (20 mL) and washed with sat.'d aq. NaHCO3 (1×10 mL). The organic layer was dried over MgSO4, filtered, and concentrated in vacuo to gave the desired N-(2-aminophenyl)-4-(dibenzylamino)benzamide: 1H NMR (600 MHz, MeOH-d4) δ 7.83 (d, J=9.0 Hz, 2H), 7.31 (m, 6H), 7.25 (m, 8H), 6.81 (d, J=9.1 Hz, 2H), 4.79 (s, 4H); cal'd 408.2 (MH+), exp 408.2 (MH+).

Workup

  1. customThe crude reaction mixture
  2. washwashed with sat.'d aq. NaHCO3 (1×10 mL)
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude residue was purified by reverse-phase chromatography (20-100% MeCN/H2O with 0.05% TFA)
  7. additiondiluted with EtOAc (20 mL)
  8. washwashed with sat.'d aq. NaHCO3 (1×10 mL)
  9. dry with materialThe organic layer was dried over MgSO4
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-115e358d5a8f4c05b2980f64ac586699
Source dataset
uspto-grants-2012_02
Patent number
US08119685B2

Reaction notes

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