Triethylamine → HCID 23081120, compound

HRID 856170Notes

Reaction equation

HRID 856170 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[CH3:6][C:7]1([CH2:18][CH2:19][CH2:20][OH:21])[O:11][C:10]2=[N:12][C:13]([N+:15]([O-:17])=[O:16])=[CH:14][N:9]2[CH2:8]1.C(N(CC)CC)C>C(Cl)Cl.CN(C)C1C=CN=CC=1>[CH3:1][S:2]([O:21][CH2:20][CH2:19][CH2:18][C:7]1([CH3:6])[O:11][C:10]2=[N:12][C:13]([N+:15]([O-:17])=[O:16])=[CH:14][N:9]2[CH2:8]1)(=[O:4])=[O:3]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 230814842-Methyl-2-(3-hydroxypropyl)-6-nitro-2,3-dihydroimidazo[2,1-b]oxazole

Product 1

HCID 23081120HCID 23081120, compoundYield 92.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

Methanesulfonyl chloride (1.4 ml, 18.09 mmol) in methylene chloride (10 ml) was added dropwise to a mixture of 2-methyl-2-(3-hydroxypropyl)-6-nitro-2,3-dihydroimidazo[2,1-b]oxazole prepared in Example 38 (2.1 g, 9.24 mmol), triethylamine (2.8 g, 20.09 mmol), 4-dimethylaminopyridine (50 mg, 0.41 mmol) and methylene chloride (80 ml) with cooling on ice-bath followed by stirring at room temperature overnight. The reaction mixture was concentrated. 10% hydrochloric acid was added to the residue, and the resulting mixture was stirred for 30 minutes with cooling on ice-bath. The precipitates were filtered off and washed with water to afford 3-(2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-yl)propyl methanesulfonate (2.6 g, yield 92%) as a white powder.

Workup

  1. temperaturewith cooling on ice-bath
  2. concentrationThe reaction mixture was concentrated
  3. addition10% hydrochloric acid was added to the residue
  4. stirringthe resulting mixture was stirred for 30 minutes
  5. temperaturewith cooling on ice-bath
  6. filtrationThe precipitates were filtered off
  7. washwashed with water

Sources & evidence

ORD record
ord-e386eef458a54867a07121c09bb91922
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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