Diazald → 1-Diazo-3-{o-[5-(2,4-dichlorophenoxy)-2-nitrophenoxy]phenoxy}-2-propanone

HRID 21524

Reaction equation

[OH-].[K+].[CH3:3][N:4]([N:15]=O)S(C1C=CC(C)=CC=1)(=O)=O.[Cl:17][C:18]1[CH:45]=[C:44]([Cl:46])[CH:43]=[CH:42][C:19]=1[O:20][C:21]1[CH:22]=[CH:23][C:24]([N+:39]([O-:41])=[O:40])=[C:25]([CH:38]=1)[O:26][C:27]1[CH:37]=[CH:36][CH:35]=[CH:34][C:28]=1[O:29][CH2:30][C:31](Cl)=[O:32]>CO.CCOCC.O1CCCC1>[N+:4](=[CH:3][C:31](=[O:32])[CH2:30][O:29][C:28]1[CH:34]=[CH:35][CH:36]=[CH:37][C:27]=1[O:26][C:25]1[CH:38]=[C:21]([O:20][C:19]2[CH:42]=[CH:43][C:44]([Cl:46])=[CH:45][C:18]=2[Cl:17])[CH:22]=[CH:23][C:24]=1[N+:39]([O-:41])=[O:40])=[N-:15]

Participants

Conditions

Temperature: 42 °C

Procedure

A mixture of potassium hydroxide in methanol (20.0 mL of a 4M solution ) is heated to 42° C. and treated dropwise with a mixture of N-methyl-N-nitroso-p-toluenesulfonamide (4 g, 18.7 mmol) in ether (40 mL). The diazomethane is distilled over, condensed with a dry ice/acetone condenser and collected. The diazomethane/ether solution is stirred in an ice-bath, treated dropwise with a solution of {o-[5-(2,4-dichlorophenoxy)-2-nitrophenoxy]phenoxy}acetyl chloride (1.09 g, 2.32 mmol) in tetrahydrofuran, stirred for 30 minutes and concentrated in vacuo to give the title product as a yellow oil which is identified by NMR spectral analyses.

Workup

distillationThe diazomethane is distilled over,
customcondensed with a dry ice/acetone condenser
customcollected
stirringstirred for 30 minutes
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-d1f6cb8854ac44ce91cca18716b94224
Source dataset: uspto-grants-1995_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05424280

Linked notes

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