Water → HCID 18183075, compound

HRID 1636977Notes

Reaction equation

HRID 1636977 reaction equation
[N:1]1[C:2]([C:12](OCC)=[O:13])=[CH:3][N:4]2[CH2:9][CH2:8][CH2:7][S:6](=[O:11])(=[O:10])[C:5]=12.[H-].C([Al+]CC(C)C)C(C)C.O>ClCCl>[N:1]1[C:2]([CH:12]=[O:13])=[CH:3][N:4]2[CH2:9][CH2:8][CH2:7][S:6](=[O:10])(=[O:11])[C:5]=12

Participants

5

Reactant 3

HCID 962WaterHCID 18183093HCID 18183093, compoundHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 18183075HCID 18183075, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-70 °C

Procedure

Ethyl 6,7-dihydro-5H-imidazo[2,1-b][1,3]thiazine-2-carboxylate-8,8-dioxide (200 mg, 0.82 mmol) was dissolved in dry dichloromethane (minimum volume) under argon and cooled to -70° C. Diisobutylaluminium hydride (1.5M in toluene, 1 ml, 1.5 mmol) was added at <-70° C. and the mixture stirred at -70° C. until thin layer chromatography and infra-red spectroscopy showed little or no starting material remaining. Water (5 ml) was added carefully, cooling removed and the mixture stirred at ambient temperature for 1 h. Celite was added to the mixture and the resulting mixture filtered through a Celite pad. The Celite pad was washed with dichloromethane and water and the filtrate and washings combined and evaporated to dryness under reduced pressure. The residue was re-evaporated with ethanol (2×), triturated under diethyl ether and the product collected by filtration, washed with diethyl ether and dried in air (274 mg, 30%) (Found: M+ 200.0256. C7H8N2O3S requires M 200.0253); νmax (Nujol) 1678, 1316, 1161 and 1191 cm-1 ; δH [250 MHz; (CD3)2SO] 2.50-2.57 (2H, m), 3.81-3.85 (2H, m), 4.31 (2H, t, J 6 Hz), 8.27 (1H, s), 9.80 (1H, s).

Workup

  1. temperaturecooling
  2. customremoved
  3. stirringthe mixture stirred at ambient temperature for 1 h
  4. additionCelite was added to the mixture
  5. filtrationthe resulting mixture filtered through a Celite pad
  6. washThe Celite pad was washed with dichloromethane and water
  7. customevaporated to dryness under reduced pressure
  8. customThe residue was re-evaporated with ethanol (2×)
  9. customtriturated under diethyl ether
  10. filtrationthe product collected by filtration
  11. washwashed with diethyl ether
  12. customdried in air (274 mg, 30%) (Found: M+ 200.0256. C7H8N2O3S requires M 200.0253)

Sources & evidence

ORD record
ord-a2f7b7f9fd3d49ccbe2decb7eed86b5b
Source dataset
uspto-grants-2000_03
Patent number
US06037469

Reaction notes

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