Morpholine → Toluene-4-thiosulfonic acid S-(3-morpholin-4-yl-propyl)ester

HRID 707675Notes

Reaction equation

HRID 707675 reaction equation
Cl[CH2:2][CH2:3][CH2:4][S:5][S:6]([C:9]1[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=1)(=[O:8])=[O:7].[NH:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[N:16]1([CH2:2][CH2:3][CH2:4][S:5][S:6]([C:9]2[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=2)(=[O:8])=[O:7])[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 11430Potassium CarbonateHCID 67607671Toluene-4-thiosulfonic acid S-(3-chloropropyl)ester

Product 1

HCID 67605844Toluene-4-thiosulfonic acid S-(3-morpholin-4-yl-propyl)ester

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Toluene-4-thiosulfonic acid S-(3-chloro-propyl) ester (61.7 g, 233 mmol, 1.00 eq.), morpholine (22.2 g, 255 mmol, 1.09 eq.) and potassium carbonate (33.8 g, 240 mmol, 1.06 eq.) were stirred together in acetonitrile (1 L) for 64 hours at 50° C. The mixture was concentrated, then partitioned between ethyl acetate and water. The organic solution was washed with water (2×), dried using MgSO4, and concentrated to produce a light yellow oil weighing 61.5 g (84%).

Workup

  1. concentrationThe mixture was concentrated
  2. custompartitioned between ethyl acetate and water
  3. washThe organic solution was washed with water (2×)
  4. customdried
  5. concentrationconcentrated
  6. customto produce a light yellow oil

Sources & evidence

ORD record
ord-5580b2adf3214d2e9afa28f9a0cdfacb
Source dataset
uspto-grants-2015_11
Patent number
US09175042B2

Reaction notes

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