Dimethyl Sulfide → HCID 15428582, compound

HRID 1421688Notes

Reaction equation

HRID 1421688 reaction equation
C1C(=O)N([Br:8])C(=O)C1.S(C)C.[O:12]=[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N:14]1[C:19]1[CH:26]=[CH:25][C:22]([CH2:23]O)=[CH:21][CH:20]=1>C(Cl)Cl>[O:12]=[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N:14]1[C:19]1[CH:26]=[CH:25][C:22]([CH2:23][Br:8])=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 1068Dimethyl SulfideHCID 67184N-bromobutanimideHCID 15428581HCID 15428581, compound

Product 1

HCID 15428582HCID 15428582, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of NBS (1.59 g, 8.94 mmol) and CH2Cl2 was cooled to 0°. To this solution (under Ar) was added Me2S (10.72 mmol, 0.78 mL) via syringe. This mixture was then cooled to -20° and added to a solution of the benzyl alcohol from Step 2 (1.2 g, 5.96 mmol) in CH2Cl2 via pipette. The reaction mixture was warmed to 0° and stirred for several hours. The residue was poured into ice water and extracted with CH2Cl2 (3×). The organic layers were combined, washed with brine, dried (MgSO4), filtered and concentrated to give the title compound as a yellow solid, which will be used in the next step without further purification.

Workup

  1. temperatureThis mixture was then cooled to -20°
  2. temperatureThe reaction mixture was warmed to 0°
  3. extractionextracted with CH2Cl2 (3×)
  4. washwashed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-c7f6616e88ad44bd87bc81fad80bbcef
Source dataset
uspto-grants-2000_06
Patent number
US06077853

Reaction notes

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