O-Phenylenediamine → HCID 74015251, compound

HRID 1182451Notes

Reaction equation

HRID 1182451 reaction equation
[CH3:1][O:2][CH:3]([C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1)[CH2:4][CH:5]=[CH:6][CH:7]=[CH:8][C:9](Cl)=[O:10].[C:20]1([NH2:27])[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[NH2:26].CN1CCOCC1>C(Cl)Cl>[NH2:26][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=1[NH:27][C:9](=[O:10])[CH:8]=[CH:7][CH:6]=[CH:5][CH2:4][CH:3]([O:2][CH3:1])[C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 7243O-PhenylenediamineHCID 79724-MethylmorpholineHCID 91207794HCID 91207794, compound

Product 1

HCID 74015251HCID 74015251, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of acid chloride 5 (115 mg,0.41 mmol) in CH2Cl2 (5 mL) at 0° C. was added 1,2-phenylenediamine (133 mg,1.23 mmol) followed by N-methylmorpholine (49 μL, 0.45 mmol). The mixture was stirred at 0° C. for 1 h, and then was allowed to warm to rt over 1 h. After being stirred for an additional 1 h at rt, the reaction mixture was partitioned between CHCl3 (2×15 mL) and water (15 mL). The combined organic layers were dried (MgSO4) and concentrated under reduced pressure to give the crude product. Purification by flash silica gel chromatography (50% ethyl acetate in hexane) afforded the desired benzamide 18 (21 mg, 15% yield): 1H NMR (300 MHz, CDCl3) δ 6.65-7.40 (m, 9H), 5.96-6.20 (m, 2H), 5.92 (d, J=15.3 Hz, 1H), 4.18 (m, 1H), 3.82 (br s, 2H), 3.81 (s, 3H ), 3.19 (s, 3H), 2.61 (m, 1H), 2.43 (m, 1H); 13CNMR (75.4 MHz,CDCl3) δ 41.7, 55.2, 56.4, 82.7, 113.8, 118.2, 119.5, 121.8, 124.4, 125.0, 127.0, 127.8, 130.1, 133.1, 139.5, 140.7, 142.4, 159.2, 164.6.

Workup

  1. temperatureto warm to rt over 1 h
  2. stirringAfter being stirred for an additional 1 h at rt
  3. customthe reaction mixture was partitioned between CHCl3 (2×15 mL) and water (15 mL)
  4. dry with materialThe combined organic layers were dried (MgSO4)
  5. concentrationconcentrated under reduced pressure
  6. customto give the crude product
  7. customPurification by flash silica gel chromatography (50% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-912c0da3cd36427bbc54d4562a854cf4
Source dataset
uspto-grants-2007_10
Patent number
US07288567B2

Reaction notes

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