Benzene → HCID 21431584, compound

HRID 436825Notes

Reaction equation

HRID 436825 reaction equation
[CH3:1][NH:2][C:3]([NH:5][C:6]1[O:10][N:9]=[C:8]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:7]=1)=[O:4].[CH2:15]([S:19]Cl)[CH2:16][CH2:17][CH3:18].C1C=CC=CC=1>N1C=CC=CC=1>[CH3:1][N:2]([S:19][CH2:15][CH2:16][CH2:17][CH3:18])[C:3]([NH:5][C:6]1[O:10][N:9]=[C:8]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:7]=1)=[O:4]

Participants

5

Reactant 3

HCID 241BenzeneHCID 3237157Urea, N-[3-(1,1-dimethylethyl)-5-isoxazolyl]-N'-methyl-HCID 108554491-butanesulfenyl chloride

Product 1

HCID 21431584HCID 21431584, compoundYield 2.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 1-methyl-3-(3-t-butyl-5-isoxazolyl)-urea (0.99 g) in pyridine (8 ml), butylsulfenyl chloride (0.67 g) is added dropwise at -30° to -40° C., and the resultant mixture is stirred at the same temperature for 6 hours. The reaction mixture is allowed to stand at room temperature overnight, poured into ice water and shaken with benzene. The organic layer is washed with 3% hydrochloric acid, 5% aqueous sodium bicarbonate solution and water in that order, dried over anhydrous sodium sulfate and evaporated to remove the solvent. The residue is chromatographed on a column of silica gel, whereby 1-methyl-1-butylthio-3-(3-t-butyl-5-isoxazolyl)urea (0.031 g) is obtained as an oil. IR: 1712, 1617 cm-1 (CC14).

Workup

  1. washThe organic layer is washed with 3% hydrochloric acid, 5% aqueous sodium bicarbonate solution and water in that order
  2. dry with materialdried over anhydrous sodium sulfate
  3. customevaporated
  4. customto remove the solvent
  5. customThe residue is chromatographed on a column of silica gel

Sources & evidence

ORD record
ord-b29b75d39efa45f69bf61d475586ee54
Source dataset
uspto-grants-1977_06
Patent number
US04028376

Reaction notes

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