1,2-Dichloroethane → (E)-3-(dimethylamino)-5-(4-hydroxy-3,5-dimethylstyryl)-N-propylbenzamide

HRID 2368879Notes

Reaction equation

HRID 2368879 reaction equation
[CH3:1][N:2]([CH3:26])[C:3]1[CH:4]=[C:5]([CH:9]=[C:10](/[CH:12]=[CH:13]/[C:14]2[CH:19]=[C:18]([CH3:20])[C:17]([O:21]COC)=[C:16]([CH3:25])[CH:15]=2)[CH:11]=1)[C:6](O)=[O:7].C(Cl)CCl.C1C=[N:35][C:34]2N(O)N=N[C:33]=2[CH:32]=1.C(N)CC>CN(C1C=CN=CC=1)C.CN(C=O)C.CCOC(C)=O>[CH3:26][N:2]([CH3:1])[C:3]1[CH:4]=[C:5]([CH:9]=[C:10](/[CH:12]=[CH:13]/[C:14]2[CH:15]=[C:16]([CH3:25])[C:17]([OH:21])=[C:18]([CH3:20])[CH:19]=2)[CH:11]=1)[C:6]([NH:35][CH2:34][CH2:33][CH3:32])=[O:7]

Participants

8

Reactant 4

HCID 111,2-DichloroethaneHCID 7852PropylamineHCID 181649HOAtHCID 67262210(E)-3-(dimethylamino)-5-(4-(methoxymethoxy)-3,5-dimethylstyryl)benzoic acid

Product 1

HCID 67256446(E)-3-(dimethylamino)-5-(4-hydroxy-3,5-dimethylstyryl)-N-propylbenzamide

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5 (80 mg, 0.225 mmol), EDC (88 mg, 0.45 mmol), HOAT (61.2 mg, 0.45 mmol), and DMAP (5.5 mg, 0.045 mmol) in 2 mL of DMF was added propylamine (37.8 □L, 0.45 mmol) at room temperature. The reaction mixture was stirred overnight (about 18 hours) and diluted with EtOAc. The solution was washed with brine and dried with Na2SO4. The solution was filtered and concentrated.

Workup

  1. washThe solution was washed with brine
  2. dry with materialdried with Na2SO4
  3. filtrationThe solution was filtered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-2202c4e260094d93a5bcdcb72b704ca9
Source dataset
uspto-grants-2014_04
Patent number
US08703815B2

Reaction notes

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