1,2-Dichloroethane → HCID 21467116, compound

HRID 1939171Notes

Reaction equation

HRID 1939171 reaction equation
[NH2:1][CH:2]1[C:8](=[O:9])[NH:7][C:6]2[CH:10]=[CH:11][CH:12]=[CH:13][C:5]=2[C:4](=[O:14])[CH2:3]1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[Cl:29][C:30]1[CH:35]=[C:34]([Cl:36])[CH:33]=[CH:32][C:31]=1[CH:37]([CH3:41])C(O)=O.C(N(CC)CC)C.[C:49](=O)(O)[O-:50].[Na+]>CN(C)C=O>[O:9]=[C:8]1[NH:7][C:6]2[CH:10]=[CH:11][CH:12]=[CH:13][C:5]=2[C:4](=[O:14])[CH2:3][CH:2]1[NH:1][C:49](=[O:50])[CH2:41][CH2:37][C:31]1[CH:32]=[CH:33][C:34]([Cl:36])=[CH:35][C:30]=1[Cl:29]

Participants

8

Reactant 6

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 14029304HCID 14029304, compoundHCID 21467111HCID 21467111, compound

Product 1

HCID 21467116HCID 21467116, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A 100 mL round bottom flask was charged with 3-amino-3,4-dihydro-1H-benzo[b]azepin-2,5-dione (4 g, 17.6 mmole), EDC (3.38 g, 17.6 mmole), HOBT (2.38 g, 17.6 mmole), 2,4-dichlorophenyl propionic acid (3.86 g, 17.6 mmole), Dimethylformamide (100 mL), and triethylamine (1.78 g, 17.6 mmole). The reaction mixture was stirred at room temperature for 1 hr. and then poured into saturated sodium bicarbonate (500 mL). The aqueous mixture was extracted with ethyl acetate (3×200 mL). The combined organics were dried over anhydrous magnesium sulfate, filtered, and concentrated at reduced pressure. The resulting solid was swished with a minimum of hot chloroform and filtered to give the product, 5.8 g (84%) mp 234°-236° C.

Workup

  1. extractionThe aqueous mixture was extracted with ethyl acetate (3×200 mL)
  2. dry with materialThe combined organics were dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated at reduced pressure
  5. filtrationfiltered
  6. customto give the product, 5.8 g (84%) mp 234°-236° C.

Sources & evidence

ORD record
ord-0f206daf01b840d293da931e1ae962bd
Source dataset
uspto-grants-1997_12
Patent number
US05696111

Reaction notes

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