Aluminium lithium hydride → HCID 24826586, compound

HRID 910984Notes

Reaction equation

HRID 910984 reaction equation
[C:1]1([S:7][C:8]2[CH:13]=[CH:12][N:11]=[C:10]([NH:14][C:15]3[S:16][CH:17]=[C:18]([CH2:20][C:21](OCC)=[O:22])[N:19]=3)[CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1.CCOCC>[C:1]1([S:7][C:8]2[CH:13]=[CH:12][N:11]=[C:10]([NH:14][C:15]3[S:16][CH:17]=[C:18]([CH2:20][CH2:21][OH:22])[N:19]=3)[CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 24826585HCID 24826585, compound

Product 1

HCID 24826586HCID 24826586, compoundYield 47.1%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Ethyl 2-(2-(4-(phenylthio)pyridin-2-ylamino)thiazol-4-yl)acetate (1.20 g, 3.23 mmol) in THF was added to a solution of 1.0 M lithium aluminum hydride (9.69 mL, 9.69 mmol) in ether and THF (50 mL) at 0° C. The reaction mixture was stirred for 40 minutes, and cooled while carefully quenching with an excess of sodium sulfate decahydrate. A small amount of anhydrous magnesium sulfate was added and the reaction mixture was stirred overnight. The reaction mixture was filtered, and the cake was washed with THF several times. The combined filtrates were concentrated and the residue was recrystallized from 3:1 ethyl acetate:hexanes (50 mL). The crystals were filtered, washed with hexanes and dried to afford 2-(2-(4-(phenylthio)pyridin-2-ylamino)thiazol-4-yl)ethanol (0.501 g, 47.1% yield) as light pink crystals/needles. 1H NMR (d6-DMSO) δ 11.11 (s, 1H), 8.08 (d, 1H), 7.53-7.61 (t, 6H), 6.73 (s, 1H), 6.57 (s, 1H), 6.56 (m, 1H), 4.58 (t, 1H), 3.65 (m, 2H), 2.69 (t, 2H).

Workup

  1. temperaturecooled
  2. customwhile carefully quenching with an excess of sodium sulfate decahydrate
  3. additionA small amount of anhydrous magnesium sulfate was added
  4. stirringthe reaction mixture was stirred overnight
  5. filtrationThe reaction mixture was filtered
  6. washthe cake was washed with THF several times
  7. concentrationThe combined filtrates were concentrated
  8. customthe residue was recrystallized from 3:1 ethyl acetate
  9. filtrationThe crystals were filtered
  10. washwashed with hexanes
  11. customdried

Sources & evidence

ORD record
ord-f094aa1f974847fc9dab664504032b27
Source dataset
uspto-grants-2011_09
Patent number
US08022222B2

Reaction notes

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