Tetrahydrofuran → HCID 178520647, 화합물

HRID 1496873

반응식

HRID 1496873 반응식
Cl.[Cl:2][C:3]1[C:7]([NH2:8])=[CH:6][NH:5][N:4]=1.O1CCCC1.C(=O)(O)[O-].[Na+].[Cl:19][CH2:20][CH2:21][C:22](Cl)=[O:23]>C(OCC)(=O)C.O>[Cl:19][CH2:20][CH2:21][C:22]([NH:8][C:7]1[C:3]([Cl:2])=[N:4][NH:5][CH:6]=1)=[O:23]

참가 물질

7

반응물 4

HCID 8028TetrahydrofuranHCID 693643-Chloropropionyl chlorideHCID 516892Sodium BicarbonateHCID 178479102HCID 178479102, 화합물

생성물 1

HCID 178520647HCID 178520647, 화합물

시약·촉매·용매 2

HCID 962Water용매HCID 8857Ethyl Acetate용매

반응 조건

온도
5 °C

실험 절차

A 250-mL 3-neck flask was charged with 3-chloro-1H-pyrazol-4-amine.hydrochloride (10.0 g, 64.9 mmol), tetrahydrofuran (50 mL), and water (50 mL). The resulting suspension was cooled to 5° C. and sodium bicarbonate (17.6 g, 210 mmol) was added, followed by dropwise addition of 3-chloropropanoyl chloride (7.33 g, 57.7 mmol) at <5° C. The reaction was stirred at <10° C. for 1 hour, at which point thin layer chromatography (TLC) [Eluent: 1:1 ethyl acetate (EtOAc)/hexane]analysis indicated the starting material was consumed and the desired product was formed. It was diluted with water (50 mL) and ethyl acetate (50 mL) and the layers separated. The aqueous layer was extracted with ethyl acetate (20 mL) and the combined organic layers were concentrated to dryness to afford a pale brown solid, which was purified by flash column chromatography using ethyl acetate as eluent. The pure fractions were concentrated to afford a white solid (9.20 g, 77%): mp: 138-140° C.; 1H NMR (400 MHz, DMSO-d6) δ 12.91 (s, 1 H), 9.68 (s, 1 H), 8.03 (d, J=1.7 Hz, 1 H), 3.85 (t, J=6.3 Hz, 2 H), 2.85 (t, J=6.3 Hz, 2 H); 13C NMR (101 MHz, DMSO-d6) δ 167.52, 130.05, 123.59, 116.48, 40.75, 37.91; EIMS m/z 207 (m+).

후처리

  1. customwas consumed

출처 및 근거

ORD 기록
ord-aad6fbdd41a5461497ece6a4fe8b0395
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09199942B2

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