Water → {7-[(Phenylsulfonyl)amino]-3,4-dihydro-2H-chromen-2-yl}methylbenzenesulfonate

HRID 49461Notes

Reaction equation

HRID 49461 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH:8]([CH2:12][OH:13])[O:9]2)=[CH:4][CH:3]=1.[C:14]1([S:20](Cl)(=[O:22])=[O:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[OH2:24]>N1C=CC=CC=1>[C:14]1([S:20]([NH:1][C:2]2[CH:11]=[C:10]3[C:5]([CH2:6][CH2:7][CH:8]([CH2:12][O:13][S:20]([C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=4)(=[O:21])=[O:24])[O:9]3)=[CH:4][CH:3]=2)(=[O:22])=[O:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 962WaterHCID 7369Benzenesulfonyl chlorideHCID 10511549(7-Aminochroman-2-yl)methanol

Product 1

HCID 20637419{7-[(Phenylsulfonyl)amino]-3,4-dihydro-2H-chromen-2-yl}methylbenzenesulfonateYield 92%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

A solution of (7-amino-2-(hydroxymethyl)chroman (0.52 g, 2.9 mmol) in pyridine is treated with a solution of phenylsulfonyl chloride (0.81 mL, 6.4 mmol) in pyridine, stirred at ambient temperature for 1 h, poured into water and extracted with ethyl acetate. The extracts are combined, washed with brine, dried over MgSO4 and concentrated in vacuo. The resultant residue is chromatographed (silica gel, ethyl acetate:hexane 1:1) to afford the title product as an off-white solid, 1.23 g (92% yield), identified by NMR and mass spectral analyses.

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe resultant residue is chromatographed (silica gel, ethyl acetate:hexane 1:1)

Sources & evidence

ORD record
ord-9486a64c97bf40d68aa16aa01f6630c9
Source dataset
uspto-grants-2004_03
Patent number
US06706757B2

Reaction notes

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