m-Chloroperbenzoic acid → HCID 21414082, compound

HRID 442283Notes

Reaction equation

HRID 442283 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[CH3:12][N:13]([S:25][C:26]([CH3:29])([CH3:28])[CH3:27])[C:14]([NH:16][C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[C:19]([Cl:24])[CH:18]=1)=[O:15]>C(Cl)Cl>[CH3:12][N:13]([S:25]([C:26]([CH3:29])([CH3:28])[CH3:27])=[O:9])[C:14]([NH:16][C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[C:19]([Cl:24])[CH:18]=1)=[O:15]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 21414076HCID 21414076, compound

Product 1

HCID 21414082HCID 21414082, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

4.3 g of 80% m-chloroperbenzoic acid dissolved in 50 ml of methylene chloride were added dropwise to a solution of 6.15 g of N-methyl-N-tert.-butylthio-N'-(3,4-dichlorophenyl)-urea in 60 ml of methylene chloride cooled to 0° C. and after stirring the mixture at 0° C. for 20 minutes, the insolubles were removed by filtration. The organic phase was washed with an aqueous saturated solution of sodium bicarbonate, then with water and dried. The solvent was distilled off under reduced pressure and the residue was crystallized from isopropyl ether to obtain 5.5 g of N-methyl-N-tert.-butylsulfinyl-N'-(3,4-dichlorophenyl)-urea melting at 118° C.

Workup

  1. customthe insolubles were removed by filtration
  2. washThe organic phase was washed with an aqueous saturated solution of sodium bicarbonate
  3. dry with materialwith water and dried
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe residue was crystallized from isopropyl ether

Sources & evidence

ORD record
ord-c5d042df81fc48bebef1ca2e961dc26c
Source dataset
uspto-grants-1977_08
Patent number
US04045209

Reaction notes

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