Sodium Hydroxide → 2-Chloro-4-nitro-3-phenoxy-1-(2,5-dichloro-4-methylthio-phenoxy)-benzene

HRID 1902587Notes

Reaction equation

[Cl:1][C:2]1[C:7](Cl)=[CH:6][CH:5]=[C:4]([N+:9]([O-:11])=[O:10])[C:3]=1[O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[Cl:19][C:20]1[CH:25]=[C:24]([CH3:26])[C:23]([Cl:27])=[CH:22][C:21]=1[SH:28].[OH-].[Na+]>CS(C)=O>[Cl:1][C:2]1[C:3]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:4]([N+:9]([O-:11])=[O:10])[CH:5]=[CH:6][C:7]=1[S:28][C:21]1[CH:22]=[C:23]([Cl:27])[C:24]([CH3:26])=[CH:25][C:20]=1[Cl:19]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 14.2 gm of 2,3-dichloro-6-nitro-1-phenoxy-benzene, 10.2 gm of 2,5-dichloro-4-methylthiophenol, 5.0 ml of 10 N sodium hydroxide and 40 ml of dimethylsulfoxide was stirred for 5 hours at 100° C. and then allowed to stand overnight at room temperature. Thereafter, the reaction mixture was admixed with 400 ml of 1 N sodium hydroxide, and the product precipitated thereby was collected and recrystallized from 150 ml of ethanol. 20.5 gm (90% of theory) of the light yellow crystalline title compound, m.p. 138°-144° C., were obtained.

Workup

waitto stand overnight at room temperature
customthe product precipitated
customthereby was collected
customrecrystallized from 150 ml of ethanol

Sources & evidence

ORD record: ord-0010a48b6c09491bb4b0383d07d11dca
Source dataset: uspto-grants-1982_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04364875

Reaction notes

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