Methanesulfonyl chloride → HCID 13375749, compound

HRID 745860Notes

Reaction equation

HRID 745860 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:23])[C:7]([OH:22])=[C:8]([C:12]3[CH:17]=[CH:16][C:15]([C:18]([O:20][CH3:21])=[O:19])=[CH:14][CH:13]=3)[O:9]2)=[CH:4][CH:3]=1.[CH3:24][S:25](Cl)(=[O:27])=[O:26]>C1C=CC=CC=1>[CH3:24][S:25]([NH:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:23])[C:7]([O:22][S:25]([CH3:24])(=[O:27])=[O:26])=[C:8]([C:12]3[CH:13]=[CH:14][C:15]([C:18]([O:20][CH3:21])=[O:19])=[CH:16][CH:17]=3)[O:9]2)=[CH:4][CH:3]=1)(=[O:27])=[O:26]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 13375743HCID 13375743, compound

Product 1

HCID 13375749HCID 13375749, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
0 °C

Procedure

2.5 g of methyl 7-amino-3-hydroxy-4'-flavonecarboxylate are put in suspension in 25 cc of anhydrous benzene. The mixture is cooled to 0° C., and 10 cc of methanesulfonic acid chloride are added drop by drop. The mixture is stirred at ambient temperature until the reaction is complete. The reaction is checked by thin-layer chromatography (benzene (90)-dioxane (25)-acetic acid (4) elution solvent). The mixture is poured into 300 cc of ice water. The precipitate is filtered, washed with water and dried. The resulting product is purified by open silica column chromatography. MP=250° C. NMR in DMSO(D6): δ=3.3 ppm, 3H, singlet, CH3 methanesulfonamido; δ=3.6 ppm, 3H, singlet, CH3L methanesulfonyloxy; δ=3.9 ppm, 3H singlet, CH3 methyl ester; δ=7.1-8.4 ppm, 7H, complex multiplet, aromatic protons; δ=10.7 ppm, 1H, dome, NH; (interchangeable with D2O).

Workup

  1. washThe reaction is checked by thin-layer chromatography (benzene (90)-dioxane (25)-acetic acid (4) elution solvent)
  2. additionThe mixture is poured into 300 cc of ice water
  3. filtrationThe precipitate is filtered
  4. washwashed with water
  5. customdried
  6. customThe resulting product is purified by open silica column chromatography

Sources & evidence

ORD record
ord-963a8399776e4fff994d65b205d1f9a6
Source dataset
uspto-grants-1986_07
Patent number
US04600788

Reaction notes

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