Dimethylformamide → HCID 20298687, compound

HRID 263101Notes

Reaction equation

HRID 263101 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:3]=1[CH:4]=[O:5].CN(C)C=O.[H-].[Na+].Cl[CH2:20][CH2:21][CH2:22][N:23]1[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1>C1(C)C=CC=CC=1>[CH3:11][O:10][C:7]1[CH:8]=[CH:9][C:2]([O:1][CH2:20][CH2:21][CH2:22][N:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)=[C:3]([CH:6]=1)[CH:4]=[O:5]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 956952-Hydroxy-5-methoxybenzaldehydeHCID 958344-(3-Chloropropyl)morpholine

Product 1

HCID 20298687HCID 20298687, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
70 °C

Procedure

A stirred solution of 25 g of 2-hydroxy-5-methoxybenzaldehyde in 125 ml. of dimethylformamide is treated portionwise with 8.2 g of 50% sodium hydride (oil dispersion). The temperature is kept below 35° C. by means of an ice-water bath. When the addition is complete, the mixture is warmed to 70° C. and cooled to 25° C. This is followed by the addition of a solution of 36 g. of N-(3-chloropropyl)morpholine in 65 ml. of toluene. The mixture is stirred and heated at 100°-105° C. for 4 hours, cooled, poured into 300 ml. of ice-water and extracted with three 150 ml. portions of ether. The combined ether layers are then extracted with 40 ml. of cold 1:1 hydrochloric acid, followed by 20 ml of water. The aqueous phases are combined, layered over with 150 ml of ether, stirred and basified with 40 g. of potassium carbonate. The layers are separated and the aqueous phase is extracted with three 100 ml portions of ether. The combined ether layers are dried over magnesium sulfate. The solvent is removed on a rotary evaporator and the residue is distilled to give 34 g. of the title compound, boiling point 180°-185° C. at 0.1-0.2 mm of Hg.

Workup

  1. customThe temperature is kept below 35° C. by means of an ice-water bath
  2. additionWhen the addition
  3. temperaturecooled to 25° C
  4. additionThis is followed by the addition of a solution of 36 g
  5. temperatureheated at 100°-105° C. for 4 hours
  6. temperaturecooled
  7. additionpoured into 300 ml
  8. extractionof ice-water and extracted with three 150 ml
  9. extractionThe combined ether layers are then extracted with 40 ml
  10. stirringstirred
  11. customThe layers are separated
  12. extractionthe aqueous phase is extracted with three 100 ml portions of ether
  13. dry with materialThe combined ether layers are dried over magnesium sulfate
  14. customThe solvent is removed on a rotary evaporator
  15. distillationthe residue is distilled
  16. customto give 34 g

Sources & evidence

ORD record
ord-a7feab3d55884cba993268a55568b86a
Source dataset
uspto-grants-1979_05
Patent number
US04156079

Reaction notes

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