Water → 4-(4-Nitroisothiazol-5-yl)morpholine

HRID 871042Notes

Reaction equation

HRID 871042 reaction equation
Br[C:2]1[S:6][N:5]=[CH:4][C:3]=1[N+:7]([O-:9])=[O:8].[NH:10]1[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1.CCN(C(C)C)C(C)C.O>O1CCOCC1>[N+:7]([C:3]1[CH:4]=[N:5][S:6][C:2]=1[N:10]1[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1)([O-:9])=[O:8]

Participants

6

Reactant 4

HCID 962WaterHCID 8083MorpholineHCID 81531DiisopropylethylamineHCID 126311735-Bromo-4-nitroisothiazole

Product 1

HCID 712617854-(4-Nitroisothiazol-5-yl)morpholine

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 5-bromo-4-nitroisothiazole (P) (500 mg, 2.39 mmol) and morpholine (6B2) (620 mg, 7.12 mmol) in dioxane (10 mL) at room temperature (25° C.) was added DIEA (851 μL, 4.78 mmol). The solution was stirred for 30 min and HPLC showed the reaction was complete. Water (10 mL) was then added. A precipitate was formed, filtered and air dried at room temperature to get the product 6C6 (500 mg, 2.32 mmol).

Workup

  1. customA precipitate was formed
  2. filtrationfiltered
  3. customair dried at room temperature
  4. customto get the product 6C6 (500 mg, 2.32 mmol)

Sources & evidence

ORD record
ord-1222045766594109a02eccc1ca989843
Source dataset
uspto-grants-2015_03
Patent number
US08969584B2

Reaction notes

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