Sodium Hydroxide → HCID 11266412, compound

HRID 2102796Notes

Reaction equation

CN([CH:4]=[C:5]1[CH2:18][CH2:17][C:8]2[N:9]=[C:10]([N:12]=CN(C)C)[S:11][C:7]=2[C:6]1=O)C.[N+]([O-])(O)=O.[C:24]1([NH:30][C:31]([NH2:33])=[NH:32])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.[OH-].[Na+]>COCCO>[C:24]1([NH:30][C:31]2[N:33]=[CH:4][C:5]3[CH2:18][CH2:17][C:8]4[N:9]=[C:10]([NH2:12])[S:11][C:7]=4[C:6]=3[N:32]=2)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of N′-(6-dimethylaminomethylene-7-oxo-4,5,6,7-tetrahydro-benzothiazol-2-yl)-N,N-dimethyl-formamidine (200 mg, 0.72 mmol), N-phenyl-guanidine nitrate (142 mg, 0.72 mmol), NaOH (57 mg, 1.44 mmol) and 2-methoxyethanol (4 mL) was heated under microwave irradiation (300 W, 100° C.) for 30 min. The reaction mixture was concentrated under vacuum. Flash column chromatography (20% EtOAc:hexane) afforded the title product as a dark yellow solid (16 mg, 8%): mp 240° C. (dec). 1H-NMR (DMSO-d6): δ 9.42 (s, 1H, NH), 8.23 (s, 1H, Py-H), 7.77 (d, 2H, J 7.7, Ph-H), 7.26 (t, 2H, J 7.7, Ph-H), 6.91 (t, 1H, J 7.2, Ph-H), 2.93 (s, 4H, CH2—CH2). MS (ESI+): m/z 296.07 (M+H)+.

Workup

concentrationThe reaction mixture was concentrated under vacuum

Sources & evidence

ORD record: ord-1b64bbb2f7544382aac9fc846b693696
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07576091B2

Reaction notes

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