Benzhydrylamine → 3-Chloro-propane-1-sulfonic acid benzhydryl-amide

HRID 1894366Notes

Reaction equation

HRID 1894366 reaction equation
O1CCCC1.[Cl:6][CH2:7][CH2:8][CH2:9][S:10](Cl)(=[O:12])=[O:11].[NH2:14][CH:15]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(N(CC)CC)C>O>[CH:15]([NH:14][S:10]([CH2:9][CH2:8][CH2:7][Cl:6])(=[O:12])=[O:11])([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 7036BenzhydrylamineHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 154103-Chloropropanesulphonyl chloride

Product 1

HCID 436538363-Chloro-propane-1-sulfonic acid benzhydryl-amideYield 118.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

In a three-neck round bottom flask equipped with argon inlet was charged with anhydrous tetrahydrofuran and 3-chloropropane sulfonyl chloride (500 mg, 2.82 mmol, Aldrich). The flask was cooled down to 0° C., and aminodiphenylmethane (0.49 mL, 2.82 mmol, Fluka) was added, followed by triethylamine (0.59 mL, 4.23 mmol). The reaction mixture was stirred at 0° C. and monitored by the thin layer chromatography. Upon completion, water was added the reaction mixture. It was concentrated then diluted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated to give 3-chloro-propane-1-sulfonic acid benzhydryl-amide (1.083 g, light brown solid). The crude product was used without further purification.

Workup

  1. customIn a three-neck round bottom flask equipped with argon inlet
  2. concentrationIt was concentrated
  3. additionthen diluted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-34c7f4a9864a49a5bc04c5f02675cac3
Source dataset
uspto-grants-2013_08
Patent number
US08513239B2

Reaction notes

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