Water → HCID 19070278, compound

HRID 1955481Notes

Reaction equation

C([O:3][C:4]([C:6]1[N:7]=[C:8]2[N:13]([CH:14]=1)[CH2:12][CH2:11][CH2:10][S:9]2)=O)C.N1C(C=O)=CN2CCCSC=12.[H-].C([Al+]CC(C)C)C(C)C.O>ClCCl>[N:7]1[C:6]([CH:4]=[O:3])=[CH:14][N:13]2[CH2:12][CH2:11][CH2:10][S:9][C:8]=12

Participants

Conditions

Temperature: -70 °C

Procedure

6,7-Dihydro-5H-imidazo[2,1-b][1,3]thiazine-2-carboxaldehyde Ethyl 6,7-dihydro-5H-imidazo[2,1-b][1,3]thiazine-2-carboxylate (2.12 g, 10 mmol) was dissolved in dry dichloromethane (40 ml) under argon and cooled to -70%. Diisobutylaluminium hydride (1.5M in toluene, 12 ml, 18 mmol) was added below -68° C. and the reaction mixture stirred at -70° C. for 1 h. Water was added carefully and the cooling removed. The reaction mixture was stirred vigorously at ambient temperature for 15 minutes and Celite (2 g) added. The mixture was filtered through Celite, the filter bed washed with dichloromethane and water, the filtrate and the washings combined and evaporated to dryness under reduced pressure. The residue was evaporated from ethanol (2×) to give the title compound as a white solid (1.31 g, 78%); nmax (CH2Cl2) 1685, 1543 and 1453 cm-1 ; dH (250MHz; CDCl3) 2.34-2.43 (2H, m), 3.20 (2H, t, J 6Hz), 4.17 (2H, t, J 6Hz) 7.58 (1H, s), 9.75 (1H, s).

Workup

temperaturecooled to -70%
customthe cooling removed
stirringThe reaction mixture was stirred vigorously at ambient temperature for 15 minutes
additionCelite (2 g) added
filtrationThe mixture was filtered through Celite
washthe filter bed washed with dichloromethane and water
customevaporated to dryness under reduced pressure
customThe residue was evaporated from ethanol (2×)

Sources & evidence

ORD record: ord-c9aef8cf37ee44e48fd4108e1756341b
Source dataset: uspto-grants-1998_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05776455

Reaction notes

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