Phenol → HCID 58006923, compound

HRID 2264051Notes

Reaction equation

HRID 2264051 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH3:22])[CH:12]([C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=3)[NH:11]S(=O)(=O)[NH:9]2)=[CH:4][CH:3]=1.C1(O)C=CC=CC=1>Br.C(O)(=O)C>[Cl:19][C:16]1[CH:17]=[CH:18][C:13]([CH:12]([NH2:11])[C:8]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)([NH2:9])[CH3:22])=[CH:14][CH:15]=1

Participants

5

Reactant 2

HCID 996PhenolHCID 58006844HCID 58006844, compound

Product 1

HCID 58006923HCID 58006923, compoundYield 50.8%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 260Hydrogen BromideSolvent

Conditions

Temperature
130 °C

Procedure

A suspension of rac-(3R*,4S*)-3,4-bis(4-chlorophenyl)-3-methyl-1,2,5-thiadiazolidine-1,1-dioxide (3.71 g, 10.4 mmol) and phenol (4.86 g, 52 mmol) in 48% hydrobromic acid (13.56 mL) and acetic acid (46.44 mL) was stirred at 130° C. for 40 min (reaction progress monitored by TLC), then allowed to cool to room temperature. The crude reaction mixture was partitioned between ethyl acetate and water, and the aqueous phase washed twice with ethyl acetate. The aqueous phase was then made basic by the slow addition of solid sodium hydroxide (60 g; CARE! Exothermic) and extracted with diethyl ether (3×500 mL). The combined ethereal extracts were washed with 2M sodium hydroxide (100 mL), then dried over anhydrous sodium sulfate (with a few pellets of solid sodium hydroxide) and evaporated to give the title compound (1.56 g). This material was carried forward to the next step without any further purification.

Workup

  1. custom(reaction progress monitored by TLC)
  2. temperatureto cool to room temperature
  3. customThe crude reaction mixture
  4. customwas partitioned between ethyl acetate and water
  5. washthe aqueous phase washed twice with ethyl acetate
  6. additionThe aqueous phase was then made basic by the slow addition of solid sodium hydroxide (60 g; CARE! Exothermic)
  7. extractionextracted with diethyl ether (3×500 mL)
  8. washThe combined ethereal extracts were washed with 2M sodium hydroxide (100 mL)
  9. dry with materialdried over anhydrous sodium sulfate (with a few pellets of solid sodium hydroxide) and
  10. customevaporated

Sources & evidence

ORD record
ord-8b4495eb2d4145888588d95cfe723b08
Source dataset
uspto-grants-2010_12
Patent number
US07851626B2

Reaction notes

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