Carbon Tetrachloride → HCID 18789704, compound

HRID 618220Notes

Reaction equation

HRID 618220 reaction equation
[C:1]([CH2:3][O:4][C:5]1[C:6]([CH3:16])=[C:7]([NH:11][S:12]([CH3:15])(=[O:14])=[O:13])[CH:8]=[CH:9][CH:10]=1)#[N:2].C(O)(C)(C)C.C(Cl)(Cl)(Cl)[Cl:23].ClOC(C)(C)C>C1(C)C=CC=CC=1>[Cl:23][C:8]1[C:7]([NH:11][S:12]([CH3:15])(=[O:14])=[O:13])=[C:6]([CH3:16])[C:5]([O:4][CH2:3][C:1]#[N:2])=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 5943Carbon TetrachlorideHCID 6386tert-ButanolHCID 521297Tert-Butyl hypochloriteHCID 18789705N-[3-(Cyanomethoxy)-2-methylphenyl]methanesulfonamide

Product 1

HCID 18789704HCID 18789704, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
-4 °C

Procedure

N-(3-cyanomethoxy-2-methylphenyl)-methanesulfonamide (1.87 g, 7.78 mmol) was suspended in a 1:1 mixture of t-butanol and carbon tetrachloride (80 ml) and cooled in an ice bath. t-Butyl hypochlorite (TCl, 0.85 g, 7.78 mmol) was added dropwise. The mixture was maintained at -4° C. overnight then warmed to room temperature. The volatiles were removed at reduced pressure. N-(6-chloro-3-cyanomethoxy-2-methylphenyl)-methanesulfonamide (1.05 g, 49% yield) was obtained by recrystallization from toluene.

Workup

  1. temperaturecooled in an ice bath
  2. temperaturethen warmed to room temperature
  3. customThe volatiles were removed at reduced pressure

Sources & evidence

ORD record
ord-cc7336778e244057b089560234c091c5
Source dataset
uspto-grants-1999_09
Patent number
US05952362

Reaction notes

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