N-Cyanoacetylethylcarbamate → (2-Cyano-2-{[3,5-dichloro-4-(5-isopropyl-1-methyl-6-oxo-1,6-dihydro-pyridazin-3-yloxy)-phenyl]-hydrazono}-acetyl)-carbamic acid ethyl ester

HRID 271200

반응식

HRID 271200 반응식
[NH2:1][C:2]1[CH:19]=[C:18]([Cl:20])[C:5]([O:6][C:7]2[CH:8]=[C:9]([CH:15]([CH3:17])[CH3:16])[C:10](=[O:14])[N:11]([CH3:13])[N:12]=2)=[C:4]([Cl:21])[CH:3]=1.[N:22]([O-])=O.[Na+].[C:26]([CH2:28][C:29]([NH:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])=[O:30])#[N:27].C([O-])(=O)C.[Na+]>C(O)(=O)C.Cl.O>[CH2:35]([O:34][C:32](=[O:33])[NH:31][C:29](=[O:30])[C:28]([C:26]#[N:27])=[N:22][NH:1][C:2]1[CH:19]=[C:18]([Cl:20])[C:5]([O:6][C:7]2[CH:8]=[C:9]([CH:15]([CH3:16])[CH3:17])[C:10](=[O:14])[N:11]([CH3:13])[N:12]=2)=[C:4]([Cl:21])[CH:3]=1)[CH3:36]

참가 물질

8

반응물 4

HCID 23112N-CyanoacetylethylcarbamateHCID 517045Sodium AcetateHCID 23668193Sodium NitriteHCID 598344456-(4-Amino-2,6-dichloro-phenoxy)-4-isopropyl-2-methyl-2H-pyridazin-3-one

생성물 1

HCID 72574122(2-Cyano-2-{[3,5-dichloro-4-(5-isopropyl-1-methyl-6-oxo-1,6-dihydro-pyridazin-3-yloxy)-phenyl]-hydrazono}-acetyl)-carbamic acid ethyl ester수율 99.7%

시약·촉매·용매 3

HCID 176Acetic Acid용매HCID 313Hydrochloric Acid용매HCID 962Water용매3회

반응 조건

온도
7.5 °C

실험 절차

A mixture of 6-(4-amino-2,6-dichloro-phenoxy)-4-isopropyl-2-methyl-2H-pyridazin-3-one (67) (10 g, 30.47 mmol) in glacial acetic acid (60 mL) and concentrated hydrochloric acid (9.06 mL) cooled to 5-10° C. was treated dropwise with a solution of sodium nitrite (2.3 g, 32.3 mmol) in water (6 mL). The reaction was stirred at 5-10° C. for 30 min. At this time, the reaction was treated with N-cyanoacetylurethane (5.34 g, 33.52 mmol) followed by a solution of sodium acetate (7.5 g, 91.41 mmol) in water (22.5 mL). The reaction was stirred at 5-10° C. for 30 min and then was diluted with water (50 mL). The resulting solids were collected by filtration, washed with a 1:1 mixture of glacial acetic acid:water (40 mL) followed by water (2×60 mL), dried under house vacuum, and then dried under vacuum at 50° C. to afford (2-cyano-2-{[3,5-dichloro-4-(5-isopropyl-1-methyl-6-oxo-1,6-dihydro-pyridazin-3-yloxy)-phenyl]-hydrazono}-acetyl)-carbamic acid ethyl ester (68) (15.04 g, 95%) as an orange solid; ES(+)-LRMS for C20H20Cl2N6O5 (M+H)+ at m/z=495. Exact Mass=494.0872; Molecular Weight=495.33.

후처리

  1. stirringThe reaction was stirred at 5-10° C. for 30 min
  2. filtrationThe resulting solids were collected by filtration
  3. washwashed with a 1:1 mixture of glacial acetic acid
  4. customdried under house vacuum
  5. customdried under vacuum at 50° C.

출처 및 근거

ORD 기록
ord-46caf830d39641898bdfd45f712c8705
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07452882B2

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