Ethyl propiolate → HCID 59497305, compound

HRID 1747288Notes

Reaction equation

HRID 1747288 reaction equation
[C:1]1([CH2:11][N:12]2[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=3[NH:14][C:13]2=[O:21])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[C:22]([O:26][CH2:27][CH3:28])(=[O:25])[C:23]#[CH:24]>CN(C=O)C.CN(C1C=CN=CC=1)C.C(OCC)(=O)C>[CH2:27]([O:26][C:22](=[O:25])/[CH:23]=[CH:24]/[N:14]1[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[N:12]([CH2:11][C:1]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH:4]=[CH:3][CH:2]=2)[C:13]1=[O:21])[CH3:28]

Participants

6

Reactant 2

HCID 12182Ethyl propiolateHCID 24071726HCID 24071726, compound

Product 1

HCID 59497305HCID 59497305, compoundYield 101.4%

Reagents, catalysts & solvents 3

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

Procedure

To a solution of 1-Naphthalen-1-ylmethyl-1,3-dihydro-benzimidazol-2-one (0.5 g, 1.8 mmol) in DMF (4 mL) were added ethyl propiolate (0.28 mL, 2.7 mmol) and DMAP (0.22 mL), 1.8 mmol). The reaction mixture was stirred at room temperature for 10 min. The reaction mixture turned dark brown in color. The reaction mixture was diluted with ethyl acetate and washed with water (×4). The organic phase was dried over Na2SO4 and concentrated to afford 0.68 g of the desired product as a dark brown foam. This crude product was used for the next reaction without further purification. LCMS (ESMS): m/z 373.33 (M+H+).

Workup

  1. washwashed with water (×4)
  2. dry with materialThe organic phase was dried over Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-51f8edc95b3b4571840fe99a4527a338
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

Loading…