Methanesulfonyl chloride → HCID 10711497, compound

HRID 1439946Notes

Reaction equation

HRID 1439946 reaction equation
[OH:1][CH2:2][C:3]1[N:4]([S:8]([C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=2)(=[O:10])=[O:9])[CH:5]=[CH:6][N:7]=1.[CH3:18][S:19](Cl)(=[O:21])=[O:20]>ClCCl.C(N(CC)CC)C.O>[CH3:18][S:19]([O:1][CH2:2][C:3]1[N:4]([S:8]([C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=2)(=[O:10])=[O:9])[CH:5]=[CH:6][N:7]=1)(=[O:21])=[O:20]

Participants

6

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 10562764HCID 10562764, compound

Product 1

HCID 10711497HCID 10711497, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
0 °C

Procedure

The alcohol described in (b) above (12.6 mg) was dissolved in dichloromethane (2.5 ml) and triethylamine (0.07 ml). This solution was cooled to 0° C. Methanesulfonyl chloride (0.04 ml) was added to the solution dropwise. After stirring for 10 mins the solution was diluted with water and the organic layer was separated, dried (MgSO4), filtered and the solvent removed in vacuo to yield a white solid which was used in the following reaction without further purification. 1H NMR (250 MHz, CDCl3) d 2.44 (3H, s, ArH), 2.94 (3H, s, SO2CH3), 5.51 (2H, s, CH2SO2), 7.08 (1H, d, J=1.5 Hz, imidazole-H), 7.40 (2H, d, J=8.0 Hz, ArH), 7.49 (1H, d, J=1.5 Hz, imidazole-H), 7.92 (2H, d, J=8.0 Hz, ArH).

Workup

  1. customthe organic layer was separated
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. customthe solvent removed in vacuo
  5. customto yield a white solid which
  6. customwas used in the following reaction without further purification

Sources & evidence

ORD record
ord-ff061d22d944442f80d18606b652b08c
Source dataset
uspto-grants-1996_03
Patent number
US05496833

Reaction notes

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