Water → 4-Thiomorpholinoaniline

HRID 450047Notes

Reaction equation

HRID 450047 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][S:13][CH2:12][CH2:11]2)=[CH:6][CH:5]=1)([O-])=O.O.C(N(CC)CC)C>C(OCC)(=O)C>[N:10]1([C:7]2[CH:6]=[CH:5][C:4]([NH2:1])=[CH:9][CH:8]=2)[CH2:11][CH2:12][S:13][CH2:14][CH2:15]1

Participants

5

Reactant 3

HCID 962WaterHCID 8471TriethylamineHCID 31247254-(4-Nitrophenyl)thiomorpholine

Product 1

HCID 107742064-ThiomorpholinoanilineYield 69.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Stannous chloride dihydrate (10 g, 44.4 mmol) was added to a solution of 4-(4-nitro-phenyl)-thiomorpholine (2 g, 8.9 mmol) in ethyl acetate and stirred at room temperature for 4 hr. Water was added and the reaction mixture was neutralized with triethyl amine. The organic layer was dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure to yield 4-thiomorpholin-4-yl-phenylamine (1.2 g, 60%) as a solid.

Workup

  1. dry with materialThe organic layer was dried over anhydrous sodium sulphate
  2. filtrationfiltered
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3ed1be4da18f40f1ba1fd6be4d4324c6
Source dataset
uspto-grants-2013_07
Patent number
US08486962B2

Reaction notes

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