Morpholine → Ethyl 2-(4-morpholinylmethyl)-1,3-thiazole-4-carboxylate

HRID 872655Notes

Reaction equation

HRID 872655 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([CH2:11]Cl)[S:9][CH:10]=1)=[O:5])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[NH:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1>CN(C=O)C.C(Cl)Cl>[O:22]1[CH2:23][CH2:24][N:19]([CH2:11][C:8]2[S:9][CH:10]=[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[N:7]=2)[CH2:20][CH2:21]1

Participants

6

Reactant 3

HCID 8083MorpholineHCID 11430Potassium CarbonateHCID 24715135Ethyl 2-(chloromethyl)-1,3-thiazole-4-carboxylate

Product 1

HCID 13121935Ethyl 2-(4-morpholinylmethyl)-1,3-thiazole-4-carboxylateYield 93%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

2-Chloromethyl-thiazole-4-carboxylic acid ethyl ester (500 mg, 2.431 mmol) and potassium carbonate (504 mg, 3.65 mmol) were dissolved in dry DMF and morpholine (0.212 ml, 2.431 mmol) was added. The reaction mixture was stirred at RT overnight, diluted with DCM and washed with NaHCO3 and water. Organic phase was evaporated to dryness to yield the title compound (93%). 1H-NMR (400 MHz; DMSO-d6): δ 1.30 (t, 3H), 2.49-2.54 (m, 4H, overlap with DMSO), 3.58-3.63 (m, 4H), 3.84 (s, 2H), 4.29 (q, 2H), 8.47 (s, 1H). m/z [256.3+1].

Workup

  1. washwashed with NaHCO3 and water
  2. customOrganic phase was evaporated to dryness

Sources & evidence

ORD record
ord-4cfb45ec9ab842108f0b28701cddc979
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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