Tetrahydrofuran → HCID 58955093, compound

HRID 1990969Notes

Reaction equation

HRID 1990969 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([CH2:9][S:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)(=[O:12])=[O:11])[CH:3]=1.O.[C:20]1(C)C=CC(S(O)(=O)=O)=CC=1.C(OCC)(OCC)OCC.CC([O-])(C)C.[K+].C1COCC1.[NH4+].[Cl-]>O.ClCCCl>[Br:1][C:2]1[CH:3]=[C:4]2[C:5](=[CH:7][CH:8]=1)[NH:6][CH:20]=[C:9]2[S:10]([C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)(=[O:11])=[O:12]

Participants

9

Reactant 6

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 31214Ethyl orthoformateHCID 521998p-Toluenesulfonic acid monohydrateHCID 23665647Potassium tert-butoxideHCID 290623094-Bromo-2-[(phenylsulfonyl)methyl]benzenamine

Product 1

HCID 58955093HCID 58955093, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 962WaterSolvent

Procedure

A stirred solution of 4-bromo-2-[(phenylsulfonyl)methyl]aniline (3.26 g, 10.00 mmol, p-toluenesulfonic acid monohydrate (0.20 g), triethyl orthoformate (8.32 mL, 50 mmol) and 1,2-dichloroethane (70 mL) is heated at reflux under nitrogen for 5 hours and then at room temperature for 16 hours. The reddish reaction is concentrated in vacuo to a red oil. The resulting crude intermediate iminoether is stirred in dry THF (50 mL) and treated with 1.0M KOtBu in THF (13 mL, 13 mmol). After 5 min, a tan precipitate is evident. After 1 hour, the reaction is treated with water (30 mL) and NH4Cl (0.60 g), extracted with CH2Cl2 (150 mL), dried (MgSO4), filtered and concentrated in vacuo to a light orange solid. Trituration with ethyl acetate and hexanes affords the title compound as a light orange solid (2.78 g, 72%). Mp: 176-178° C. MS (ES−): 334 (M−H).

Workup

  1. temperatureat reflux under nitrogen for 5 hours
  2. customThe reddish reaction
  3. concentrationis concentrated in vacuo to a red oil
  4. waitAfter 5 min
  5. waitAfter 1 hour
  6. extractionextracted with CH2Cl2 (150 mL)
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo to a light orange solid

Sources & evidence

ORD record
ord-f6cfe41dd7714e458674f2d953837921
Source dataset
uspto-grants-2010_01
Patent number
US07645752B2

Reaction notes

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