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

HRID 2368870Notes

Reaction equation

HRID 2368870 reaction equation
COC[O:4][C:5]1[C:21]([CH3:22])=[CH:20][C:8](/[CH:9]=[CH:10]/[C:11]2[CH:12]=[C:13]([CH:17]=[CH:18][CH:19]=2)[C:14]([OH:16])=O)=[CH:7][C:6]=1[CH3:23].C(Cl)CCl.O[N:29]1[C:33]2N=CC=[CH:37][C:32]=2N=N1.C(N)CC>CN(C1C=CN=CC=1)C.CN(C=O)C.CCOC(C)=O>[OH:4][C:5]1[C:6]([CH3:23])=[CH:7][C:8](/[CH:9]=[CH:10]/[C:11]2[CH:12]=[C:13]([CH:17]=[CH:18][CH:19]=2)[C:14]([NH:29][CH2:33][CH2:32][CH3:37])=[O:16])=[CH:20][C:21]=1[CH3:22]

Participants

8

Reactant 4

HCID 111,2-DichloroethaneHCID 7852PropylamineHCID 181649HOAtHCID 67262065(E)-3-(4-(methoxymethoxy)-3,5-dimethylstyryl)benzoic acid

Product 1

HCID 53250516(E)-3-(4-hydroxy-3,5-dimethylstyryl)-N-propylbenzamide

Reagents, catalysts & solvents 3

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

Procedure

To a solution of (E)-3-(4-(methoxymethoxy)-3,5-dimethylstyryl)benzoic acid (0.1 g, 0.32 mmol), EDC (0.125 g, 0.64 mmol), 1-hydroxy-7-azabenzo-triazole (HOAT; 87.1 mg, 0.64 mmol), and DMAP (7.8 mg, 0.064 mmol) in 2 mL of DMF was added propylamine (54 μL, 0.64 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-cc1c6a77e7cf49ddb3f36aabe9d46393
Source dataset
uspto-grants-2014_04
Patent number
US08703815B2

Reaction notes

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