Chloroform → HCID 54093297, compound

HRID 356518Notes

Reaction equation

HRID 356518 reaction equation
[S:1](Br)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].CCN(CC)CC.[CH3:19][C:20]([O:23][C:24]([N:26]([C:34]1[CH:39]=[C:38]([C:40]([CH3:43])([CH3:42])[CH3:41])[C:37]([SH:44])=[CH:36][C:35]=1[CH3:45])[C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])=[O:25])([CH3:22])[CH3:21].C(Cl)(Cl)Cl>C(Cl)(Cl)(Cl)Cl>[CH3:33][C:30]([O:29][C:27]([N:26]([C:34]1[CH:39]=[C:38]([C:40]([CH3:43])([CH3:42])[CH3:41])[C:37]([S:44][S:1]([C:4]2[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=2)(=[O:3])=[O:2])=[CH:36][C:35]=1[CH3:45])[C:24]([O:23][C:20]([CH3:19])([CH3:21])[CH3:22])=[O:25])=[O:28])([CH3:31])[CH3:32]

Participants

6

Reactant 4

HCID 6212ChloroformHCID 8471TriethylamineHCID 101308854-Methylbenzene-1-sulfonyl bromideHCID 10786892HCID 10786892, compound

Product 1

HCID 54093297HCID 54093297, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent2×

Procedure

A solution of tosyl bromide (17.1 g, 72.73 mmol) and NEt3 (7.36 g, 72.73 mmol) in CCl4 (250 mL) was cooled to 0° C. To this solution was added [5-(1,1-dimethylethyl)-4-mercapto-2-methylphenyl]-imidodicarbonic acid bis(1,1-dimethylethyl) ester obtained from Example FFFF in CCl4 (250 mL) dropwise over an 8 hour period. The mixture was then allowed to warm to room temperature overnight. Chloroform was added, and the solution was washed with H2O and brine, dried (Na2SO4), filtered and concentrated. The resulting material was flash chromatographed on silica gel, eluting with 4:1 CHCl3 :hexanes to afford the title compound. 1H NMR (CDCl3) δ 1.16 (s, 9 H), 1.40 (s, 18 H), 2.10 (s, 3 H), 2.40 (s, 3 H), 7.07 (s, 1 H), 7.19 (d, 2 H), 7.40 (s, 1 H), 7.44 (d, 2 H).

Workup

  1. washthe solution was washed with H2O and brine
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customchromatographed on silica gel
  6. washeluting with 4:1 CHCl3

Sources & evidence

ORD record
ord-9be0b84e7aca4f46987c5918996cfe41
Source dataset
uspto-grants-1998_11
Patent number
US05834506

Reaction notes

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