Diethyl Ether → HCID 86585266, compound

HRID 2113429Notes

Reaction equation

HRID 2113429 reaction equation
[CH2:1]([N:5]1[CH:9]=[CH:8][N:7]=[CH:6]1)[CH2:2][CH2:3][CH3:4].[C:10]1([CH3:23])[CH:15]=[C:14]([CH3:16])[CH:13]=[C:12]([CH3:17])[C:11]=1[S:18]([O:21][NH2:22])(=[O:20])=[O:19].CCOCC>C(Cl)Cl>[C:10]1([CH3:23])[CH:15]=[C:14]([CH3:16])[CH:13]=[C:12]([CH3:17])[C:11]=1[S:18]([O-:21])(=[O:20])=[O:19].[CH2:1]([N+:5]1[CH:9]=[CH:8][N:7]([NH2:22])[CH:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 61347ButylimidazoleHCID 11830845O-(2,4,6-Trimethylbenzenesulfonyl)hydroxylamine

Product 1

HCID 86585266HCID 86585266, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

An ice-cold solution of 1-butylimidazole (7.0 g, 16.30 mmol) in anhydrous CH2Cl2 (35 mL) was treated dropwise with a solution of O-mesitylene sulfonylhydroxylamine (17.8 g, 16.50 mmol) in CH2Cl2 (70 mL). After stirring for 6 hours in the ice-bath, ether (210 mL) was added with stirring over the course of 1 hour. The resulting mixture was allowed to stand at −16° C. overnight. The product was recovered by filtration, and washed with a mixture of CH2Cl2: ether (3:1 v/v) to yield a white amorphous powder; 16.70 g. The crude product was recrystallized from a mixture of CH2Cl2 (80 mL) and ether (80 mL) to give 12.40 g; mp 71-73° C.

Workup

  1. additionwas added
  2. waitto stand at −16° C. overnight
  3. filtrationThe product was recovered by filtration
  4. washwashed with a mixture of CH2Cl2: ether (3:1 v/v)
  5. customto yield a white amorphous powder
  6. customThe crude product was recrystallized from a mixture of CH2Cl2 (80 mL) and ether (80 mL)
  7. customto give 12.40 g

Sources & evidence

ORD record
ord-3b63b07ad6dc4b52b454a0d2f1ab8457
Source dataset
uspto-grants-2008_10
Patent number
US07432254B2

Reaction notes

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