Hydrochloric Acid → 2-Chloro-5-[2,3-dichloro-4-(2-propen-1-yloxy)benzoyl]-N-[(dimethylamino)methylene]benzenesulfonamide

HRID 482649Notes

Reaction equation

HRID 482649 reaction equation
[CH2:1](Br)[CH:2]=[CH2:3].[OH:5][C:6]1[CH:28]=[CH:27][C:9]([C:10]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([S:19]([N:22]=[CH:23][N:24]([CH3:26])[CH3:25])(=[O:21])=[O:20])[CH:13]=2)=[O:11])=[C:8]([Cl:29])[C:7]=1[Cl:30].C(=O)([O-])[O-].[K+].[K+].Cl>CN(C)C=O>[CH2:1]([O:5][C:6]1[CH:28]=[CH:27][C:9]([C:10]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([S:19]([N:22]=[CH:23][N:24]([CH3:26])[CH3:25])(=[O:20])=[O:21])[CH:13]=2)=[O:11])=[C:8]([Cl:29])[C:7]=1[Cl:30])[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 54479825HCID 54479825, compound

Product 1

HCID 704559262-Chloro-5-[2,3-dichloro-4-(2-propen-1-yloxy)benzoyl]-N-[(dimethylamino)methylene]benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5.6 g (40 mmol) of allyl bromide are added dropwise, with magnetic stirring, to a mixture of 13.1 g (30 mmol) of 4-hydroxy-3'-dimethylaminomethyleneaminosulfonyl-2,3,4'-trichlorobenzophenone, 5.0 g (36 mmol) of ground potassium carbonate and 50 ml of dry dimethylformamide at room temperature, and the mixture is stirred for about 8 hours. The pale yellow suspension is then stirred in portions into a mixture of 400 ml of ice-water and 100 ml of 2N hydrochloric acid, and the precipitate is filtered off. Colorless crystals, melting point 141°-142° C. (from acetone/ethanol).

Workup

  1. filtrationthe precipitate is filtered off

Sources & evidence

ORD record
ord-74b998e1e2d44538a6796b2721c2b849
Source dataset
uspto-grants-1986_03
Patent number
US04574128

Reaction notes

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