Morpholine → 4-Chloro-2-morpholin-4-yl-1,3-thiazole-5-carbonitrile

HRID 2091699Notes

Reaction equation

HRID 2091699 reaction equation
Cl[C:2]1[S:3][C:4]([C:8]#[N:9])=[C:5]([Cl:7])[N:6]=1.C(N(CC)C(C)C)(C)C.[NH:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1>C(O)C.O>[Cl:7][C:5]1[N:6]=[C:2]([N:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)[S:3][C:4]=1[C:8]#[N:9]

Participants

6

Reactant 3

HCID 8083MorpholineHCID 81531DiisopropylethylamineHCID 155763592,4-Dichloro-5-cyanothiazole

Product 1

HCID 592500134-Chloro-2-morpholin-4-yl-1,3-thiazole-5-carbonitrileYield 95.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

2,4-dichloro-5-cyanothiazole (1.26 g, 0.00704 mol) and N,N-diisopropylethylamine (3.68 mL, 0.0211 mol) were dissolved in ethanol at 70° C. Morpholine (0.614 mL, 0.0704 mol) was added to the hot solution and the mixture was stirred for 30 minutes, cooled down to rt, diluted with water (50 mL) and the formed precipitate was collected to give the title compound (1.55 g, 91%). LCMS: (FA) ES+, 230. 1H NMR (300 MHz, d6-DMSO) δ: 3.71-3.67 (m, 4H), 3.52-3.48 (m, 4H).

Workup

  1. customthe formed precipitate was collected

Sources & evidence

ORD record
ord-535d736ad8034887aadbb81912ba3c02
Source dataset
uspto-grants-2013_05
Patent number
US08440664B2

Reaction notes

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