Dimethyl Sulfoxide → HCID 12881149, compound

HRID 1902585Notes

Reaction equation

HRID 1902585 reaction equation
[Cl:1][C:2]1[C:7](Cl)=[CH:6][C:5]([O:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[C:4]([N+:16]([O-:18])=[O:17])[CH:3]=1.[Cl:19][C:20]1[CH:25]=[C:24]([Cl:26])[C:23]([Cl:27])=[CH:22][C:21]=1[OH:28].[OH-].[Na+].CS(C)=O>C(Cl)(Cl)Cl.O>[Cl:1][C:2]1[CH:3]=[C:4]([N+:16]([O-:18])=[O:17])[C:5]([O:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:6][C:7]=1[O:28][C:21]1[CH:22]=[C:23]([Cl:27])[C:24]([Cl:26])=[CH:25][C:20]=1[Cl:19]

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 72712,4,5-TrichlorophenolHCID 14798Sodium HydroxideHCID 13102542HCID 13102542, compound

Product 1

HCID 12881149HCID 12881149, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 28.4 gm of 4,5-dichloro-2-nitro-1-phenoxy-benzene, 21.6 gm of 2,4,5-trichloro-phenol, 10 ml of 10 N sodium hydroxide and 80 ml of dimethylsulfoxide was stirred for 6 hours at 150° C. and then allowed to stand overnight at room temperature. Thereafter, the reaction mixture was stirred into 600 ml of water, the aqueous mixture was made alkaline, and the precipitated reaction product was taken up in chloroform. The organic phase was washed with water, dried and evaporated, and the residue was recrystallized from 200 ml of ethanol, yielding 43 gm (97% of theory) of the light yellow crystalline title compound, m.p. 84° C.

Workup

  1. waitto stand overnight at room temperature
  2. customthe precipitated reaction product
  3. washThe organic phase was washed with water
  4. customdried
  5. customevaporated
  6. customthe residue was recrystallized from 200 ml of ethanol

Sources & evidence

ORD record
ord-9cc5f6a3101b4526bf410e36f37e588b
Source dataset
uspto-grants-1982_12
Patent number
US04364875

Reaction notes

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