Dimethylformamide → HCID 20298674, compound

HRID 2049966Notes

Reaction equation

HRID 2049966 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+].[CH3:19][N:20]([CH3:25])[CH2:21][CH2:22][CH2:23]Cl>C1(C)C=CC=CC=1>[CH3:19][N:20]([CH3:25])[CH2:21][CH2:22][CH2:23][O:1][C:2]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:3]=1[CH:4]=[O:5]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 669603-Chloro-N,N-dimethyl-1-propanamineHCID 956952-Hydroxy-5-methoxybenzaldehyde

Product 1

HCID 20298674HCID 20298674, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2-Hydroxy-5-methoxybenzaldehyde (31.2 g) in 170 ml. of dimethylformamide is treated first with 10.1 g of 50% sodium hydride, then with 160 ml. of a 2 N toluene solution of 3-dimethylaminopropyl chloride, following the procedure described in Example 1A, yielding 34.1 g of the title compound, boiling point 149°-155° C. at 0.2-0.3 mm of Hg.

Sources & evidence

ORD record
ord-111da2d4f42d4aa9aa81b893dcdc1af1
Source dataset
uspto-grants-1980_04
Patent number
US04199528

Reaction notes

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