2-Morpholinoethylamine → 2-Methyl-5-{[2-(4-morpholinyl)ethyl]amino}1,3-benzothiazole-4,7-dione

HRID 1727237Notes

Reaction equation

HRID 1727237 reaction equation
[NH2:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][O:7][CH2:6][CH2:5]1.CO[C:12]1[C:21](=[O:22])[C:16]2[N:17]=[C:18]([CH3:20])[S:19][C:15]=2[C:14](=[O:23])[CH:13]=1>C(O)C>[CH3:20][C:18]1[S:19][C:15]2[C:14](=[O:23])[CH:13]=[C:12]([NH:1][CH2:2][CH2:3][N:4]3[CH2:9][CH2:8][O:7][CH2:6][CH2:5]3)[C:21](=[O:22])[C:16]=2[N:17]=1

Participants

4

Reactant 2

HCID 4082852-MorpholinoethylamineHCID 4817565-Methoxy-2-methylbenzo[d]thiazole-4,7-dione

Product 1

HCID 101496202-Methyl-5-{[2-(4-morpholinyl)ethyl]amino}1,3-benzothiazole-4,7-dione

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

51.2 μl (0.39 mmol; 3 equivalents) of 4-(2-aminoethyl)morpholine is added to 27 mg (0.129 mmol) of 5-methoxy-2-methyl-4,7-dioxobenzothiazole in solution in 2 ml of anhydrous ethanol. The reaction mixture is stirred under reflux for 18 hours then the solvent is evaporated off under reduced pressure. The residue is purified on a silica column (eluent: 5% methanol in dichloromethane). The expected compound is obtained in the form of a red powder.

Workup

  1. temperatureunder reflux for 18 hours
  2. customthe solvent is evaporated off under reduced pressure
  3. customThe residue is purified on a silica column (eluent: 5% methanol in dichloromethane)

Sources & evidence

ORD record
ord-79f2feceb9124468b5e30ec2cf5e75f1
Source dataset
uspto-grants-2009_02
Patent number
US07495021B2

Reaction notes

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