Water → HCID 178424720, compound

HRID 330251Notes

Reaction equation

HRID 330251 reaction equation
[S:1](Cl)(Cl)=[O:2].[OH:5][N:6]=[C:7]([NH2:17])[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([CH3:15])=[C:11]([CH3:16])[CH:10]=1.N1C=CC=CC=1.O>C(Cl)Cl>[CH3:16][C:11]1[CH:10]=[C:9]([CH2:8][C:7]2[NH:17][S:1](=[O:2])[O:5][N:6]=2)[CH:14]=[CH:13][C:12]=1[CH3:15]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 24386Thionyl ChlorideHCID 51878672-(3,4-dimethylphenyl)-N'-hydroxyethanimidamide

Product 1

HCID 178424720HCID 178424720, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Thionyl chloride (17.7 mL, 0.24 mol) in methylene chloride (40 mL) was added dropwise to a solution of N'-hydroxy-2-(3,4-dimethylphenyl)ethanimidamide (10.8 g, 0.06 mol), methylene chloride (130 mL) and pyridine (9.8 mL, 0.12 mol) at 5° C. After 3 hours, the mixture was poured into water and the organic layer separated. The organic layer was washed with saturated aqueous sodium chloride, dried over magnesium sulfate and concentrated in vacuo. Recrystallization from ethyl ether afforded the desired product (4.3 g, 32%) as an off-white solid, m.p. 127°-130° C.

Workup

  1. customthe organic layer separated
  2. washThe organic layer was washed with saturated aqueous sodium chloride
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customRecrystallization from ethyl ether

Sources & evidence

ORD record
ord-0e20db68441d462ca599154f46ff4ffb
Source dataset
uspto-grants-1990_01
Patent number
US04895862

Reaction notes

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