Methanesulfonyl chloride → HCID 673827, compound

HRID 1360639Notes

Reaction equation

HRID 1360639 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][CH2:7][NH2:8])=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.[CH3:20][S:21](Cl)(=[O:23])=[O:22]>C(Cl)Cl>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][CH2:7][NH:8][S:21]([CH3:20])(=[O:23])=[O:22])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 674302-(4-Chlorophenyl)ethylamineHCID 81531Diisopropylethylamine

Product 1

HCID 673827HCID 673827, compoundYield 98.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-5 °C

Procedure

A solution of 4-chlorophenethylamine (5.0 g, 32 mmol) and DIEA (6.0 ml, 35 mmol) in anhydrous DCM (100 ml) was cooled at −5° C. and methanesulfonyl chloride (2.75 ml, 35 mmol) was added dropwise. The resulting mixture was stirred at −5° C. for 1 hour. Then the reaction mixture was washed with a 1N aqueous solution of HCl (2×100 ml) and a saturated aqueous solution of NaHCO3 (100 ml). The aqueous layers were extracted with DCM (100 ml). The organic layers were combined, dried (MgSO4) and the solvent was removed under reduced pressure to give 7.4 g (98%) of the title compound as a pale yellow powder. HPLC, Rt: 2.6 min (purity: 95.1%). LC/MS, M+(ESI): 234.1, M−(ESI): 232.1.

Workup

  1. washThen the reaction mixture was washed with a 1N aqueous solution of HCl (2×100 ml)
  2. extractionThe aqueous layers were extracted with DCM (100 ml)
  3. dry with materialdried (MgSO4)
  4. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-d68bcbfc78684718b6570979e3a89839
Source dataset
uspto-grants-2011_02
Patent number
US07879876B2

Reaction notes

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