Methanol → 4-Morpholinecarbothioamide

HRID 2258187Notes

Reaction equation

HRID 2258187 reaction equation
[N:1]1([C:7]2[S:8]C=C(CO)[N:11]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.CO>C(Cl)(Cl)Cl>[NH2:11][C:7]([N:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1)=[S:8]

Participants

4

Reactant 2

HCID 887Methanol2×HCID 10608093[2-(Morpholin-4-yl)-1,3-thiazol-4-yl]methanol

Product 1

HCID 23935444-MorpholinecarbothioamideYield 65%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

Using the procedure of Example 9C but replacing 2-(N,N-dimethylamino)-4-(hydroxymethyl)thiazole with 2-(4-morpholinyl)-4-(hydroxymethyl)thiazole provided, after silica gel chromatography using 1% methanol in chloroform, the desired compound, Rf 0.54 (4% methanol in chloroform), in 65% yield. 1H NMR (CDCl3) δ0.97 (d, J=7 Hz, 3H), 1.00 (d, J=7 Hz, 3H), 2.25 (m, 1H), 3.50 (dd, J=5, 4 Hz, 2H), 3.76 (s, 3H), 3.84 (dd, J=5, 4 Hz, 2H), 4.67 (dd, J=9, 5 Hz, 1H), 7.63 (br d, 1H), 8.02 (s, 1H).

Workup

  1. customprovided

Sources & evidence

ORD record
ord-bff2a789ed1949159cf8edc315b4e1b4
Source dataset
uspto-grants-1997_08
Patent number
US05659044

Reaction notes

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