1-Butanesulfonyl chloride → Butane-1-sulfonic acid 6-chloro-2-oxo-2H-1-benzopyran-4-yl ester

HRID 495142Notes

Reaction equation

HRID 495142 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][C:7](=[O:12])[CH:6]=[C:5]2[OH:13].CCN(C(C)C)C(C)C.[CH2:23]([S:27](Cl)(=[O:29])=[O:28])[CH2:24][CH2:25][CH3:26]>C(Cl)Cl>[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[O:8][C:7](=[O:12])[CH:6]=[C:5]([O:13][S:27]([CH2:23][CH2:24][CH2:25][CH3:26])(=[O:29])=[O:28])[C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 754301-Butanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 546863486-Chloro-4-hydroxycoumarin

Product 1

HCID 11301544Butane-1-sulfonic acid 6-chloro-2-oxo-2H-1-benzopyran-4-yl esterYield 25.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

6-Chloro-4-hydroxycoumarin (0.455 mmol, 0.090 g) is suspended in 5 mL DCM. DIEA (1.37 mmol, 0.237 mL) is added and the reaction is cooled to 0° C. 1-Butanesulfonyl chloride (0.5 mmol, 64.8 μL) is dissolved in DCM is added and and the reaction is stirred at ambient temperature for 2 hrs. The DCM is removed under reduced pressure and the residue is redissolved in MeOH/H2O then is purified by HPLC to afford the title compound (36.2 mg, 25%) 1H NMR (DMSO-d6, 300 MHz) δ 7.81 (2H, m), 7.56 (1H, d, J=8.75 Hz), 6.59 (1H, s), 3.99 (2H, m), 1.83 (2H, m), 1.46 (2H, m), 0.92 (3H, t, J=7.25 Hz); MS (ESI, Pos.) calcd for C13H13ClO5S m/z [M+H]=317.0, found 317.1.

Workup

  1. additionis added
  2. customThe DCM is removed under reduced pressure
  3. dissolutionthe residue is redissolved in MeOH/H2O
  4. customthen is purified by HPLC

Sources & evidence

ORD record
ord-dc392f59e2324e7bb409672b481f6f57
Source dataset
uspto-grants-2009_05
Patent number
US07538233B2

Reaction notes

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