Phenylmethanesulfonyl chloride → HCID 86690638, compound

HRID 1505603Notes

Reaction equation

HRID 1505603 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH2:9])=[C:4]([F:10])[CH:3]=1.C(N(CC)C(C)C)(C)C.[C:20]1([CH2:26][S:27](Cl)(=[O:29])=[O:28])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>ClCCl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH:9][S:27]([CH2:26][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)(=[O:29])=[O:28])=[C:4]([F:10])[CH:3]=1

Participants

5

Reactant 3

HCID 74740Phenylmethanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 3770848(4-Bromo-2-fluorophenyl)methanamine

Product 1

HCID 86690638HCID 86690638, compoundYield 80.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (4-bromo-2-fluoro-phenyl)methanamine (3 g, 14.7 mmol) in dichloromethane (50 mL) was added N,N-diisopropylethylamine (3.3 mL, 19.1 mmol), followed by phenylmethanesulfonyl chloride (3.3 g, 17.6 mmol) and the reaction was stirred at ambient temperature for 3 hours. The reaction was diluted with dichloromethane and washed with water and brine, dried with MgSO4, concentrated and purified by silica gel column chromatography (20-100% EtOAc in heptane) to give N-[(4-bromo-2-fluoro-phenyl)methyl]-1-phenyl-methanesulfonamide (4.22 g, 80% yield). LCMS (m/z) ES+ 358 [M+1]+.

Workup

  1. washwashed with water and brine
  2. dry with materialdried with MgSO4
  3. concentrationconcentrated
  4. custompurified by silica gel column chromatography (20-100% EtOAc in heptane)

Sources & evidence

ORD record
ord-093b96b34b344a55ab55902bbbb8cf3f
Source dataset
uspto-grants-2015_12
Patent number
US09216988B2

Reaction notes

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