Dimethylformamide → HCID 19001403, compound

HRID 2259616Notes

Reaction equation

HRID 2259616 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][CH:6]=1)=[CH2:4].[Cl:12][C:13]1[CH:14]=[C:15]([OH:21])[C:16](=[CH:19][CH:20]=1)[CH:17]=[O:18].C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>O>[Cl:12][C:13]1[CH:20]=[CH:19][C:16]([CH:17]=[O:18])=[C:15]([O:21][CH2:2][C:3]([C:5]2[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][CH:6]=2)=[CH2:4])[CH:14]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 5201014-Chloro-2-hydroxybenzaldehydeHCID 112532501-(3-Bromoprop-1-en-2-yl)-4-chlorobenzene

Product 1

HCID 19001403HCID 19001403, compoundYield 106.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 19.2 g (0.083 mol) of the product from Step A, 10.0 g (0.064 mol) of 4-chlorosalicylaldehyde, 17.6 g (0.13 mol) of potassium carbonate and 64 mL of DMF was stirred at RT for 72 h. Resulting mixture treated with 125 mL of H2O and filtered. Solids were washed with several portions of H2O and dried in a vacuum oven at 40° C. to give 21.0 g of a brown solid. 1H NMR (CDCl3, 200 MHz) δ4.99 (s, 2H), 5.51 (s, 1H), 5.65 (s, 1H), 7.04-7.07 (m, 2H), 7.25-7.45 (m, 4H), 7.77 (d, 1H), 10.28 (s, 1H).

Workup

  1. customResulting mixture
  2. filtrationfiltered
  3. washSolids were washed with several portions of H2O
  4. customdried in a vacuum oven at 40° C.

Sources & evidence

ORD record
ord-59428ec073bd4029a82719204c497311
Source dataset
uspto-grants-1995_12
Patent number
US05474998

Reaction notes

Loading…