Thiomorpholine → HCID 10309451, compound

HRID 1581468Notes

Reaction equation

HRID 1581468 reaction equation
C([O:8][C:9](=O)[NH:10][C:11]1[S:15][C:14]2[C:16]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[CH:17][CH:18]=[C:19]([O:20][CH3:21])[C:13]=2[CH:12]=1)C1C=CC=CC=1.[NH:29]1[CH2:34][CH2:33][S:32][CH2:31][CH2:30]1>O1CCOCC1>[CH3:21][O:20][C:19]1[C:13]2[CH:12]=[C:11]([NH:10][C:9]([N:29]3[CH2:34][CH2:33][S:32][CH2:31][CH2:30]3)=[O:8])[S:15][C:14]=2[C:16]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 67164ThiomorpholineHCID 20724759HCID 20724759, compound

Product 1

HCID 10309451HCID 10309451, compoundYield 47.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A stirred solution of (4-methoxy-7-phenyl-benzo[b]thiophen-2-yl)-carbamic acid benzyl ester (200 mg, 0.513 mmol) in dioxane (5 ml) was heated with thiomorpholine (10 eq., 5.13 mmol) for 68 h at reflux under argon. After cooling the reaction the solvents were evaporated and the residue was chromatographed over silica gel eluting with heptane/EtOAc (1:2). The product fractions were then combined, evaporated and dried under vacuum at 60° C. to afford the pure title product (94 mg, 47% yield) as a light brown solid MS m/e=383.2 (M−H).

Workup

  1. temperatureat reflux under argon
  2. temperatureAfter cooling
  3. customthe reaction the solvents
  4. customwere evaporated
  5. customthe residue was chromatographed over silica gel eluting with heptane/EtOAc (1:2)
  6. customevaporated
  7. customdried under vacuum at 60° C.

Sources & evidence

ORD record
ord-3c336c25985544c88bd3ab57bdcd5ec3
Source dataset
uspto-grants-2004_05
Patent number
US06730670B2

Reaction notes

Loading…