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

HRID 872655
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HRID 872655 반응식
[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
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참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6344
Dichloromethane
용매

실험 절차

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].

후처리

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

출처 및 근거

ORD 기록
ord-4cfb45ec9ab842108f0b28701cddc979
출처 데이터셋
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08975254B2

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