Triethylamine → HCID 22628388, compound

HRID 278445Notes

Reaction equation

HRID 278445 reaction equation
[Br:1][CH2:2][CH:3]1[CH2:7][C:6]2[CH:8]=[C:9]([NH2:12])[CH:10]=[CH:11][C:5]=2[O:4]1.[CH3:13][S:14](Cl)(=[O:16])=[O:15].CCN(CC)CC>C(Cl)Cl>[Br:1][CH2:2][CH:3]1[CH2:7][C:6]2[CH:8]=[C:9]([NH:12][S:14]([CH3:13])(=[O:16])=[O:15])[CH:10]=[CH:11][C:5]=2[O:4]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 226283482-(Bromomethyl)-2,3-dihydro-5-benzofuranamine

Product 1

HCID 22628388HCID 22628388, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(RS)-2-bromomethyl-2,3-dihydro-benzofuran-5-ylamine (410 mg, 1.80 mmol), methansulfonyl-chloride (206 mg, 1.8 mmol), Et3N (182 mg, 1.80 mmol) were dissolved in CH2Cl2 (50 ml) and stirred overnight at room temperature. Solvent was then evaporated and the residue was chromatographed over SiO2 (Merck 230-400 mesh) eluting with CH2Cl2—MeOH (95:5) to provide (RS)-N-(2-bromomethyl-2,3-dihydro-benzofuran-5-yl)-methansulfonamide (516 mg, 94%) as an oil. MS: m/e=305.9 (M−H+)

Workup

  1. customSolvent was then evaporated
  2. customthe residue was chromatographed over SiO2 (Merck 230-400 mesh)
  3. washeluting with CH2Cl2—MeOH (95:5)

Sources & evidence

ORD record
ord-4db15550b23a45669e0e3bf669cff8c8
Source dataset
uspto-grants-2002_03
Patent number
US06359138B1

Reaction notes

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