Triethylamine → N-(3-bromopropyl)(phenyl)methanesulfonamide

HRID 517291Notes

Reaction equation

HRID 517291 reaction equation
[C:1]1([CH2:7][S:8](Cl)(=[O:10])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br.[Br:13][CH2:14][CH2:15][CH2:16][NH2:17].CCN(CC)CC>C1COCC1>[Br:13][CH2:14][CH2:15][CH2:16][NH:17][S:8]([CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)(=[O:10])=[O:9]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 74740Phenylmethanesulfonyl chlorideHCID 787013-Bromopropylamine hydrobromide

Product 1

HCID 43133750N-(3-bromopropyl)(phenyl)methanesulfonamideYield 92.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of phenylmethanesulfonyl chloride (2.19 g, 10 mmol) was added into a suspension of 3-bromopropan-1-amine hydrobromide (2.19 g, 10 mmol) and Et3N (2.02 g, 20 mmol) in THF (50 mL) at 0° C. The mixture was stirred at 0° C. for 5 min. TLC confirmed the completion of reaction. Solid was filtered out with suction, and the filtrate was concentrated to provide compound N-(3-bromopropyl)(phenyl)methanesulfonamide (2.7 g, quant.) as a pale yellow solid which was used in the next step without further purification. 1H NMR (300 MHz, CDCl3) δ 7.40 (m, 5H), 4.48 (m, 1H), 4.27 (s, 2H), 3.41 (t, J=6.6 Hz, 2H), 3.16 (q, 2H), 2.01 (m, 2H). LCMS (ESI), m/z, 314 and 316 [M+Na]+, Br pattern found.

Workup

  1. customthe completion of reaction
  2. filtrationSolid was filtered out with suction
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-e69f2315004843b9ac7a36f2b33fb448
Source dataset
uspto-grants-2015_08
Patent number
US09115101B2

Reaction notes

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