Ethyl 2-(morpholin-4-yl)-1,3-thiazole-4-carboxylate → 4-Morpholinecarbothioamide

HRID 2258186Notes

Reaction equation

HRID 2258186 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[N:7]1([C:13]2[S:14]C=C(C(OCC)=O)[N:17]=2)[CH2:12][CH2:11][O:10][CH2:9][CH2:8]1>C1(C)C=CC=CC=1.C1COCC1>[NH2:17][C:13]([N:7]1[CH2:12][CH2:11][O:10][CH2:9][CH2:8]1)=[S:14]

Participants

5

Reactant 2

HCID 15053544Ethyl 2-(morpholin-4-yl)-1,3-thiazole-4-carboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 23935444-MorpholinecarbothioamideYield 83.6%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 7.0 ml (7.0 mmol) of lithium aluminum hydride in toluene was diluted with 10 ml of THF, cooled to 0° C., and treated with a solution of 1.7 g (7.0 mmol) of ethyl 2-(4-morpholinyl)thiazole-4-carboxylate in 25 ml of THF. The resulting solution was stirred for 1 h, quenched cautiously with aqueous Rochelle's salts, diluted with chloroform, filtered, dired over Na2SO4, and concentrated in vacuo. Silica gel chromatography using 2-4% methanol in chloroform provided 856 mg (61%) of the desired compound, Rf 0.16 (4% methanol in chloroform). 1H NMR (CDCl3) δ2.44 (br, 1H), 3.46 (t, J=5 Hz, 4H), 3.81 (t, J=5 Hz, 1H), 4.55 (br s, 2H), 6.45 (s, 1H). Mass spectrum: (M+H)+ =200.

Workup

  1. customquenched cautiously with aqueous Rochelle's salts
  2. additiondiluted with chloroform
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-56d6cde692004a439740ab1590665f52
Source dataset
uspto-grants-1997_08
Patent number
US05659044

Reaction notes

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