Triethylamine → HCID 22733429, compound

HRID 2084566Notes

Reaction equation

HRID 2084566 reaction equation
CS(Cl)(=O)=O.[CH3:6][O:7][C:8]1[CH:9]=[CH:10][C:11]2[S:15][C:14]([CH2:16][C:17]3(O)C4C[CH:20]5[CH2:21][CH:22](C[CH:18]3[CH2:19]5)[CH2:23]4)=[N:13][C:12]=2[CH:28]=1.C(N(CC)CC)C>ClCCl.C(OCC)(=O)C>[CH2:18]1[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:17]1=[CH:16][C:14]1[S:15][C:11]2[CH:10]=[CH:9][C:8]([O:7][CH3:6])=[CH:28][C:12]=2[N:13]=1

Participants

6

Reactant 3

HCID 8471Triethylamine2×HCID 31297Methanesulfonyl chloride2×HCID 22733408HCID 22733408, compound2×

Product 1

HCID 22733429HCID 22733429, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

187 μl of methanesulfonyl chloride are added to a mixture of 350 mg of 2-(5-methoxybenzothiazol-2-ylmethyl)cycloheptan-2-ol (formula IX), 665 μl of triethylamine and a catalytical amount of 4-N,N-dimethylaminopyridine in 12 ml of dry dichloromethane at about 0°. The mixture is stirred for about 12 hours at room temperature, 187 μl of methansulfonyl chloride and 665 μl of triethylamine are added and the resultant reaction mixture is stirred at about 40° for about 48 hours. The mixture is diluted with 100 ml of ethyl acetate and then extracted with 1 M aqueous hydrochloric acid, saturated aqueous sodium bicarbonate solution and brine. The organic phase is dried and the solvent is evaporated off. The residue is subjected to chromatography. The title compound is obtained [13C-NMR (125.8 MHz): 166.528, 158.978, 155.645, 154.597, 126.878, 121.337, 119.750, 114.743, 105.127, 55.561, 39.394, 33.143, 29.921, 29.344, 28.775, 26.435],

Workup

  1. customat about 0°
  2. customthe resultant reaction mixture
  3. stirringis stirred at about 40° for about 48 hours
  4. extractionextracted with 1 M aqueous hydrochloric acid, saturated aqueous sodium bicarbonate solution and brine
  5. customThe organic phase is dried
  6. customthe solvent is evaporated off

Sources & evidence

ORD record
ord-08ce70a986514e199f49316ee06bd98f
Source dataset
uspto-grants-2004_04
Patent number
US06716865B1

Reaction notes

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