Methanesulfonyl chloride → HCID 66915646, compound

HRID 656484Notes

Reaction equation

HRID 656484 reaction equation
O[CH2:2][CH2:3][CH2:4][C:5]1([C:18]2[N:19]=[CH:20][NH:21][CH:22]=2)[C:14]2[C:9](=[CH:10][C:11]([O:15][CH3:16])=[CH:12][CH:13]=2)[O:8][C:7](=[O:17])[CH2:6]1.C(N(C(C)C)C(C)C)C.CS(Cl)(=O)=O.S([O-])(=O)(=O)C>ClCCl.O>[CH3:16][O:15][C:11]1[CH:10]=[C:9]2[O:8][C:7](=[O:17])[CH2:6][C:5]3([CH2:4][CH2:3][CH2:2][N:19]4[CH:20]=[N:21][CH:22]=[C:18]34)[C:14]2=[CH:13][CH:12]=1

Participants

7

Reactant 4

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 85257MethanesulfonateHCID 178487333HCID 178487333, compound

Product 1

HCID 66915646HCID 66915646, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 1.20 mmol of 4-(3-hydroxypropyl)-4-(1H-imidazol-4-yl)-7-methoxychroman-2-one and 1.44 mmol of N-ethyldiisopropylamine in 10 ml of dichloromethane is admixed dropwise at room temperature with 1.20 mmol of methanesulphonyl chloride and the reaction mixture is subsequently stirred for 3 hours. The conversion to the mesylate intermediate is observed by means of HPLC. The reaction mixture is poured into 10 ml of water and subjected to extraction and the aqueous phase is re-extracted with dichloromethane (2×). The combined organic phases are washed with brine, dried over sodium sulphate and evaporated (bath temperature: 30° C.). The residue is taken up in 10 ml of acetonitrile and heated at boiling on an oil bath for about 20 hours. The reaction mixture is left to cool and then evaporated. From the residue the title compound is identified by means of flash chromatography (SiO2 60F) on the basis of the Rf value.

Workup

  1. extractionsubjected to extraction
  2. extractionthe aqueous phase is re-extracted with dichloromethane (2×)
  3. washThe combined organic phases are washed with brine
  4. dry with materialdried over sodium sulphate
  5. customevaporated (bath temperature: 30° C.)
  6. temperatureheated
  7. waitat boiling on an oil bath for about 20 hours
  8. waitThe reaction mixture is left
  9. temperatureto cool
  10. customevaporated

Sources & evidence

ORD record
ord-dcb6dc67bcdb4027a6e1b8832ad0b036
Source dataset
uspto-grants-2011_12
Patent number
US08071774B2

Reaction notes

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