Potassium Carbonate → 9H-Thioxanthen-9-one, 1-[[2-(dimethylamino)ethyl]amino]-4-nitro-

HRID 1380614Notes

Reaction equation

HRID 1380614 reaction equation
[CH3:1][N:2]([CH3:6])[CH2:3][CH2:4][NH2:5].Cl[C:8]1[C:21]2[C:20](=[O:22])[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[S:13][C:12]=2[C:11]([N+:23]([O-:25])=[O:24])=[CH:10][CH:9]=1.C([O-])([O-])=O.[K+].[K+]>C1(C)C(C)=CC=CC=1>[CH3:1][N:2]([CH3:6])[CH2:3][CH2:4][NH:5][C:8]1[C:21]2[C:20](=[O:22])[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[S:13][C:12]=2[C:11]([N+:23]([O-:25])=[O:24])=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 66053N,N-Dimethylethylenediamine2×HCID 12909396HCID 12909396, compound

Product 1

HCID 3296019H-Thioxanthen-9-one, 1-[[2-(dimethylamino)ethyl]amino]-4-nitro-Yield 85.6%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent2×

Procedure

A solution of 9.3 g (0.105 mole) of N,N-dimethylethylenediamine in 35 ml of xylene was added dropwise over ten minutes to a stirred mixture of 1-chloro-4-nitrothioxanthone (24.5 g, 0.084 mole) and K2CO3 (12.2 g, 0.088 mole) in 350 ml of xylene. The mixture was heated for one hour at 70°, an additional 1.8 g (0.088 mole) of N,N-dimethylethylendiamine was added, and heating was continued for an additional hour. The mixture was cooled and the solid was collected, washed with cold xylene, petroleum ether, dried, triturated with water, and dried in vacuo at 70° to give the product (24.7 g) as a yellow solid, mp 177°-179°.

Workup

  1. temperatureThe mixture was heated for one hour at 70°
  2. temperatureheating
  3. waitwas continued for an additional hour
  4. temperatureThe mixture was cooled
  5. customthe solid was collected
  6. washwashed with cold xylene, petroleum ether
  7. customdried
  8. customtriturated with water
  9. customdried in vacuo at 70°

Sources & evidence

ORD record
ord-5da7bd0770b34a0f955ea7401c71917a
Source dataset
uspto-grants-1986_04
Patent number
US04582851

Reaction notes

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