Triethylamine → toluene-4-thiosulfonic acid S-(2-tert-butyl-4-dimethylsulfamoyloxy-5-methyl-phenyl) ester

HRID 1003866Notes

Reaction equation

HRID 1003866 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.[C:19]([C:23]1[C:24]([SH:37])=[CH:25][C:26]([CH3:36])=[C:27]([O:29][S:30](=[O:35])(=[O:34])[N:31]([CH3:33])[CH3:32])[CH:28]=1)([CH3:22])([CH3:21])[CH3:20]>C(Cl)(Cl)(Cl)Cl>[C:19]([C:23]1[CH:28]=[C:27]([O:29][S:30](=[O:34])(=[O:35])[N:31]([CH3:32])[CH3:33])[C:26]([CH3:36])=[CH:25][C:24]=1[S:37][S:1]([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2])([CH3:22])([CH3:21])[CH3:20]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 101308854-Methylbenzene-1-sulfonyl bromideHCID 10662229Dimethyl-sulfamic acid 5-tert-butyl-4-mercapto-2-methyl-phenyl ester

Product 1

HCID 10695175toluene-4-thiosulfonic acid S-(2-tert-butyl-4-dimethylsulfamoyloxy-5-methyl-phenyl) ester

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent2×

Conditions

Temperature
0 °C

Procedure

To a round bottom flask equipped with a magnetic stirrer and addition funnel were added tosyl bromide (1.64 g, 7.0 mmol), CCl4 (25 mL), and NEt3 (0.98 mL, 7.0 mmol). The ensuing slurry was then cooled to 0° C. A solution of 1.07 g (3.5 mmol) of dimethyl-sulfamic acid 5-tert-butyl-4-mercapto-2-methyl-phenyl ester (prepared in Example TTT) in CCl4 (25 mL) was added dropwise to the slurry. Addition was complete in 1.0 hour. After addition was complete, the ice bath was removed and the reaction was stirred at room temperature overnight. The mixture was diluted with CH2Cl2, washed with brine, dried (MgSO4), and concentrated. The residue was taken up in a small amount of EtOAc and triturated with hexane. The product was filtered and dried under high vacuum to yield the title compound. 1H NMR (CDCl3) δ 1.15 (s, 9 H), 2.23 (s, 3 H), 2.37 (s, 3 H), 3.02 (s, 6 H), 7.19 (d, 2 H), 7.22 (s, 1 H), 7.33 (s, 1 H), 7.40 (d, 2 H).

Workup

  1. customTo a round bottom flask equipped with a magnetic stirrer and addition funnel
  2. additionAddition
  3. additionAfter addition
  4. customthe ice bath was removed
  5. additionThe mixture was diluted with CH2Cl2
  6. washwashed with brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated
  9. customtriturated with hexane
  10. filtrationThe product was filtered
  11. customdried under high vacuum

Sources & evidence

ORD record
ord-57abfc2ce99f44349305ab8118f98ffd
Source dataset
uspto-grants-2000_04
Patent number
US06046355

Reaction notes

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