Water → HCID 4469917, compound

HRID 517290Notes

Reaction equation

HRID 517290 reaction equation
C([O-])([O-])=O.[K+].[K+].[C:7]1([CH2:13][S:14](Cl)(=[O:16])=[O:15])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.Br.[Br:19][CH2:20][CH2:21][NH2:22].O>C(Cl)Cl>[Br:19][CH2:20][CH2:21][NH:22][S:14]([CH2:13][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)(=[O:16])=[O:15]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 74740Phenylmethanesulfonyl chlorideHCID 27742172-Bromoethylamine hydrobromide

Product 1

HCID 4469917HCID 4469917, compoundYield 81.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

K2CO3 (8.7 g, 62 mmol) was added into a mixture of phenylmethanesulfonyl chloride (6 g, 31 mmol) and 2-bromoethanamine hydrobromide (6.4 g, 31 mmol) in DCM (100 mL) at 0° C. And the resulting mixture was stirred at r.t. for 4 hours and left standing overnight. Upon the completion of reaction, water (100 mL) was added in and DCM phase was separated. The aqueous phase was extracted with DCM. The combined organic phase was dried over Na2SO4, filtered and concentrated in vacuo to provide a crude which was separated with column chromatography (silica gel with 200-300 mesh, 0 to 50% of EtOAc in petroleum ether) to provide compound N-(2-bromoethyl)(phenyl)methanesulfonamide (7.0 g, 80%) as a pale yellow solid. 1H NMR (300 MHz, CDCl3) δ 7.40 (m, 5H), 4.58 (m, 1H), 4.29 (s, 2H), 3.34-3.29 (m, 4H). LCMS (ESI), 300, 302 [M+Na]+, Br pattern found.

Workup

  1. waitleft
  2. waitstanding overnight
  3. customwas separated
  4. extractionThe aqueous phase was extracted with DCM
  5. dry with materialThe combined organic phase was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto provide a crude which
  9. customwas separated with column chromatography (silica gel with 200-300 mesh, 0 to 50% of EtOAc in petroleum ether)

Sources & evidence

ORD record
ord-f54f86dfa11a4e7596aebf8fedfbd036
Source dataset
uspto-grants-2015_08
Patent number
US09115101B2

Reaction notes

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