Dimethylformamide dimethyl acetal → HCID 68415050, compound

HRID 2102795Notes

Reaction equation

HRID 2102795 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[C:10](=[O:11])[CH2:9][CH2:8][CH2:7][C:5]=2[N:6]=1.CO[CH:14](OC)[N:15]([CH3:17])[CH3:16]>CCO>[CH3:14][N:15]([CH:17]=[C:9]1[CH2:8][CH2:7][C:5]2[N:6]=[C:2]([N:1]=[CH:14][N:15]([CH3:17])[CH3:16])[S:3][C:4]=2[C:10]1=[O:11])[CH3:16]

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 5878502-Amino-4,5,6,7-tetrahydro-1,3-benzothiazol-7-one

Product 1

HCID 68415050HCID 68415050, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 2-amino-5,6-dihydro-4H-benzothiazol-7-one (0.5 g, 3 mmol) and N,N-dimethylformamide dimethyl acetal (1.96 mL, 1.76 g, 14.8 mmol) in EtOH (2 mL) was heated under microwave irradiation (300 W, 150° C.) for 30 min. The mixture was concentrated under vacuum before purification by flash column chromatography (50% EtOAc:hexane) to afford the title product as a tan solid (0.49 g, 59%): mp 185-186° C. Anal. RP-HPLC: tR 9.3 min (0-60% MeCN, purity 100%). 1H-NMR (CDCl3): δ 8.23 (s, 1H, CH), 7.44 (s, 1H, CH), 3.13 (s, 3H, CH3), 3.11 (s, 3H, CH3), 3.08 (s, 6H, N(CH3)2), 3.00 (t, 2H, J 6.6, CH2), 2.83 (t, 2H, J 6.6, CH2). MS (ESI+): m/z 279.15 (M+H)+.

Workup

  1. concentrationThe mixture was concentrated under vacuum before purification by flash column chromatography (50% EtOAc:hexane)

Sources & evidence

ORD record
ord-20ea656adb774bd5a4f28fbc01de654f
Source dataset
uspto-grants-2009_08
Patent number
US07576091B2

Reaction notes

Loading…