Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dimethylamine | HCID 674 | — |
| Reactant | 1,1'-Carbonyldiimidazole | HCID 68263 | — |
| Reactant | 1,8-Diazabicyclo(5.4.0)undec-7-ene | HCID 81184 | — |
| Reactant | 2-Amino-4,5,6,7-tetrahydro-1,3-benzothiazol-7-one | HCID 587850 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | HCID 86653428 | HCID 86653428 | — |
Reaction Steps
A mixture of 2-amino-5,6-dihydro-4H-benzothiazol-7-one (10 g, 59 mmol), DBU (18 mL, 0.12 mol) and CDI (24 g, 0.15 mol) in 400 mL acetonitrile is stirred for 5 h at 100° C. Then dimethylamine (150 mL, 2M in THF) is added and the reaction mixture is stirred overnight at 100° C. The reaction mixture is concentrated under reduced pressure and the residue is poured in water. The mixture is acidified to pH 5 with 6 M HCl in water and extracted with ethyl acetate. The combined organic phases are dried over MgSO4 and concentrated under reduced pressure. The residue is triturated with diethyl ether. Yield: 9.1 g.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08304556B2 |
|---|
| Source dataset | uspto-grants-2012_11 |
|---|
| ORD ID | ord-b25ff7917f834e4fbec0d38ecf05c7ea |
|---|
| Source note | uspto-grants-2012_11 |
|---|
