Ethanolamine → HCID 66672990, compound

HRID 423554

Reaction equation

HRID 423554 reaction equation
[Br:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([S:9](Cl)(=[O:11])=[O:10])=[C:4]([F:13])[CH:3]=1.[NH2:14][CH2:15][CH2:16][OH:17].C(N(CC)CC)C>C(Cl)Cl>[Br:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([S:9]([NH:14][CH2:15][CH2:16][OH:17])(=[O:11])=[O:10])=[C:4]([F:13])[CH:3]=1

Participants

5

Reactant 3

HCID 700EthanolamineHCID 8471TriethylamineHCID 5745904-Bromo-2,5-difluorobenzenesulfonyl Chloride

Product 1

HCID 66672990HCID 66672990, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 4-bromo-2,5-difluorobenzenesulfonyl chloride (1.17 g, 4 mmol) in CH2Cl2 (3 mL) was added to a solution of 2-aminoethanol (0.36 mL, 6 mmol) and triethylamine (1.67 mL, 12 mmol) in CH2Cl2 (12 mL) at ambient temperature. The mixture was stirred at ambient temperature for 1 h and concentrated. The crude product was purified by chromatography on a silica gel column using 0 to 10% MeOH/CH2Cl2 to give 884 mg (70%) of 4-bromo-2,5-difluoro-N-(2-hydroxyethyl)benzenesulfonamide as a white solid. 1H NMR (400 MHz, CDCl3): δ 7.67 (dd, 1H, Ja=7.2 Hz, Jb=6.0 Hz), 7.47 (dd, 1H, Ja=8.7 Hz, Jb=5.1 Hz), 5.39-5.14 (m, 1H), 3.78-3.64 (m, 2H), 3.26-3.10 (m, 2H), 1.73 (bs, 1H); LRMS (ESI), m/z 314/316 (M−H).

Workup

  1. concentrationconcentrated
  2. customThe crude product was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-87786cc817af465faaa129b5807fca39
Source dataset
uspto-grants-2012_01
Patent number
US08101634B2

Linked notes

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