Dimethylamine → HCID 86724060, compound

HRID 1519140Notes

Reaction equation

HRID 1519140 reaction equation
[CH3:1][NH:2][CH3:3].C(N(CC)CC)C.[Br:11][C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:13]=1[CH2:19][CH2:20][S:21](Cl)(=[O:23])=[O:22]>C1COCC1.CCOC(C)=O>[Br:11][C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:13]=1[CH2:19][CH2:20][S:21]([N:2]([CH3:3])[CH3:1])(=[O:23])=[O:22]

Participants

6

Reactant 3

HCID 674DimethylamineHCID 8471TriethylamineHCID 75412272HCID 75412272, compound

Product 1

HCID 86724060HCID 86724060, compoundYield 99.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of dimethylamine (1.91 mL of 2 M, 3.82 mmol) and triethylamine (386.7 mg, 532.6 μL, 3.82 mmol) in THF (8.1 mL) at room temperature was added 2-(2-bromo-5-chloro-phenyl)ethanesulfonyl chloride (405.0 mg, 1.27 mmol) and the mixture stirred for 10 min. The mixture was diluted with EtOAc and washed subsequently with water and brine, the organic layer dried (MgSO4) and concentrated to afford 2-(2-bromo-5-chlorophenyl)-N,N-dimethylethanesulfonamide as a white solid (413 mg, 99%). 1H NMR (500 MHz, d6-DMSO) δ 7.66 (1H, d), 7.60 (1H, s), 7.30 (1H, d), 3.31-3.34 (2H, m), 3.08-3.12 (2H, m).

Workup

  1. washwashed subsequently with water and brine
  2. dry with materialthe organic layer dried (MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-c859a25a27fc4b25b4ccfa43ca0ef8c7
Source dataset
uspto-grants-2015_07
Patent number
US09073875B2

Reaction notes

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