Triethylamine → HCID 17811098, compound

HRID 1839321Notes

Reaction equation

HRID 1839321 reaction equation
C(N(CC)CC)C.[CH3:8][S:9](Cl)(=[O:11])=[O:10].[NH2:13][CH2:14][C:15]1[N:16]=[CH:17][N:18]2[CH:22]=[CH:21][S:20][C:19]=12>ClCCl>[CH3:8][S:9]([NH:13][CH2:14][C:15]1[N:16]=[CH:17][N:18]2[CH:22]=[CH:21][S:20][C:19]=12)(=[O:11])=[O:10]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 23449290HCID 23449290, compound

Product 1

HCID 17811098HCID 17811098, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Triethylamine (0.18 ml) and 0.075 ml of methanesulfonyl chloride were added in that order under ice cooling to a solution of 134 mg of 7-aminomethylimidazo[5,1-b]thiazole in 2.5 ml of dry dichloromethane. In this state, the system was stirred for 2 hr while gradually raising the temperature to room temperature. The reaction solution was diluted with 20 ml of dichloromethane, followed by washing with saturated brine. The aqueous layer was extracted with 10 ml of dichloromethane. The organic layers were combined together, dried over anhydrous magnesium sulfate, and filtered. The solvent was removed by distillation. The oil thus obtained was purified using Sephadex LH-20 (dichloromethane:methanol=1:1) to give 30 mg of 7-(methanesulfonylaminomethyl)imidazo[5,1-b]thiazole as a light yellow solid.

Workup

  1. washby washing with saturated brine
  2. extractionThe aqueous layer was extracted with 10 ml of dichloromethane
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customThe solvent was removed by distillation
  6. customThe oil thus obtained
  7. customwas purified

Sources & evidence

ORD record
ord-66776d5482a940e09ce565b5cae87676
Source dataset
uspto-grants-2004_01
Patent number
US06677331B2

Reaction notes

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