Thiomorpholine → HCID 15158821, compound

HRID 1087117Notes

Reaction equation

HRID 1087117 reaction equation
[O:1]1[CH2:3][CH:2]1[CH2:4][O:5][C:6]1[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[CH:8][CH:7]=1.[NH:14]1[CH2:19][CH2:18][S:17][CH2:16][CH2:15]1>CC(O)C>[OH:1][CH:2]([CH2:3][N:14]1[CH2:19][CH2:18][S:17][CH2:16][CH2:15]1)[CH2:4][O:5][C:6]1[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 67164ThiomorpholineHCID 27643014-(2-Oxiranylmethoxy)benzenecarbonitrile

Product 1

HCID 15158821HCID 15158821, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of 4-(oxiranylmethoxy)benzonitrile (10 g, 56.8 mmol) and thiomorpholine (7 g, 67.8 mmol) in 2-propanol (100 ml) was stirred over night at room temperature. Solvent was evaporated. The oily residue was dissolved in hydrochloric acid (2M, 50 ml) and extracted twice with diethylether. The acid aqueous solution was treated with sodium carbonate solution. The basic-aqueous layer was extracted three times with methylene chloride. The combined organic layers were dried over magnesium sulphate and solvent was evaporated. The crude oil was crystallized from diisopropylether; methylene chloride (9:1). Yield of the title compound (8.85 g; 56%) as colourless crystals with mp. 94°-95° C.

Workup

  1. customSolvent was evaporated
  2. dissolutionThe oily residue was dissolved in hydrochloric acid (2M, 50 ml)
  3. extractionextracted twice with diethylether
  4. additionThe acid aqueous solution was treated with sodium carbonate solution
  5. extractionThe basic-aqueous layer was extracted three times with methylene chloride
  6. dry with materialThe combined organic layers were dried over magnesium sulphate and solvent
  7. customwas evaporated
  8. customThe crude oil was crystallized from diisopropylether

Sources & evidence

ORD record
ord-92a25ba560e04faf9e17717e5d6efc34
Source dataset
uspto-grants-1991_07
Patent number
US05034411

Reaction notes

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