Morpholine → HCID 7110122, compound

HRID 706240Notes

Reaction equation

HRID 706240 reaction equation
Cl[C:2]1[S:3][C:4]2[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:5]=2[N:6]=1.[NH:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1.C(N(CC)CC)C>C(O)C>[CH3:12][O:11][C:9]1[CH:8]=[CH:7][C:5]2[N:6]=[C:2]([N:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)[S:3][C:4]=2[CH:10]=1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 8471TriethylamineHCID 2731322-Chloro-6-methoxybenzothiazole

Product 1

HCID 7110122HCID 7110122, compoundYield 97.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-chloro-6-methoxy-benzothiazole (9.96 g, 0.05 mol), morpholine (10.86 mL, 0.12 mol) and triethylamine (13.9 mL, 0.10 mol) in ethanol (75 mL) was refluxed for twenty-one hours before it was cooled to room temperature and concentrated in vacuo. The residue was partitioned between dichloromethane and water. The organic layer was dried over anhydrous sodium sulfate and concentrated in vacuo to give the title compound as a light yellow solid (12.23 g): MS: (+) m/z 251 (M+1)

Workup

  1. temperaturewas refluxed for twenty-one hours before it
  2. concentrationconcentrated in vacuo
  3. customThe residue was partitioned between dichloromethane and water
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5868f66b2b2d43d09e8ec4931dfdfab2
Source dataset
uspto-grants-2015_11
Patent number
US09174976B2

Reaction notes

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