Tetrahydrofuran → 5-Cyanomethyl-4-methyl-3-oxothiomorpholine

HRID 483109Notes

Reaction equation

HRID 483109 reaction equation
C([N:3](CC)CC)C.[CH3:8][NH:9][C:10](=[O:13])[CH2:11][SH:12].O1[CH2:18][CH2:17][CH2:16][CH2:15]1>O>[C:18]([CH2:17][CH:16]1[N:9]([CH3:8])[C:10](=[O:13])[CH2:11][S:12][CH2:15]1)#[N:3]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 4047279Acetamide, 2-mercapto-N-methyl-

Product 1

HCID 135901135-Cyanomethyl-4-methyl-3-oxothiomorpholine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of omega-cyano-allyl bromide (9.07 g) in tetrahydrofurane (60 ml) cooled at -65° C. is added a mixture of triethylamine (9.5 ml) and thioglycolic methylamide (6.13 ml). After 15 minutes, cooling is stopped and the mixture is warmed to 0° C. The mixture is diluted with water and extracted with ethyl acetate. The extract is washed with water, dried, and concentrated to give 5-cyanomethyl-4-methyl-3-oxothiomorpholine (6.86 g).

Workup

  1. additionis added
  2. temperaturecooling
  3. extractionextracted with ethyl acetate
  4. washThe extract is washed with water
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-f2f875b9e1b44ee1bf768e8bf112f391
Source dataset
uspto-grants-1986_03
Patent number
US04578378

Reaction notes

Loading…