p-Bromobenzenesulfonyl chloride → HCID 4378537, compound

HRID 423562Notes

Reaction equation

HRID 423562 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH3:12][O:13][CH2:14][CH2:15][NH2:16].C(N(CC)CC)C>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:16][CH2:15][CH2:14][O:13][CH3:12])(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7396p-Bromobenzenesulfonyl chlorideHCID 80182-MethoxyethylamineHCID 8471Triethylamine

Product 1

HCID 4378537HCID 4378537, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Bromo-N-[2-(methoxy)ethyl]benzenesulfonamide (512 mg, 87%) was prepared as a white solid from 4-bromobenzenesulfonyl chloride (511 mg, 2 mmol), 2-(methoxy)ethylamine (0.174 mL, 2 mmol) and triethylamine (0.836 mL, 6 mmol) in CH2Cl2 (10 mL) in a manner similar to Example 108, Step 1. 1H NMR (400 MHz, CDCl3): δ 7.77-7.67 (m, 2H), 7.66-7.59 (m, 2H), 4.86 (t, 1H, J=5.7 Hz), 3.45-3.34 (m, 2H), 3.25 (s, 3H), 3.14-3.04 (m, 2H); LRMS (ESI), m/z 294/296 (M+H).

Sources & evidence

ORD record
ord-6c3345a8a0d144c4a13f24ba7fe0d0ab
Source dataset
uspto-grants-2012_01
Patent number
US08101634B2

Reaction notes

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