Dimethylamine → 3-(3,3-Dimethylureido)-chromone

HRID 128442Notes

Reaction equation

HRID 128442 reaction equation
[CH3:1][NH:2][CH3:3].[N:4]([C:7]1[C:16](=[O:17])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[O:9][CH:8]=1)=[C:5]=[O:6]>C1(C)C=CC=CC=1>[CH3:1][N:2]([CH3:3])[C:5](=[O:6])[NH:4][C:7]1[C:16](=[O:17])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[O:9][CH:8]=1

Participants

4

Reactant 2

HCID 674DimethylamineHCID 124645043-Isocyanatochromone

Product 1

HCID 541547243-(3,3-Dimethylureido)-chromoneYield 33.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
25 °C

Procedure

A solution of anhydrous dimethylamine (7.5 g) in dry toluene (100 ml) is added rapidly to a solution of 3-isocyanatochromone (13 g) in toluene (50 ml). The temperature of the reaction mixture rapidly rises from 20° to 47° C. and crystallization then takes place. The mixture is stirred for a further 20 minutes until the temperature of the reaction medium drops to about 25° C. After filtration, recrystallization from isopropyl ether (1,000 ml) and drying, 3-(3,3-dimethylureido)-chromone (5.4 g), which melts at 148° C., is obtained.

Workup

  1. customrapidly rises from 20° to 47° C.
  2. customcrystallization
  3. filtrationAfter filtration, recrystallization from isopropyl ether (1,000 ml)
  4. customdrying

Sources & evidence

ORD record
ord-aebaff0e492344e1840a99bbbf18cb60
Source dataset
uspto-grants-1981_03
Patent number
US04259506

Reaction notes

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