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Sodium Formate → 4-Chloro-2-formylamino-6-methyl-10,10-dioxo-10,11-dihydro-5-oxa-10lambda*6*-thia-dibenzo[a,d]cycloheptene-8-carboxylic acid ethyl ester

HRID 2425082
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Druckvorschau

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Reaktionsgleichung von HRID 2425082
[CH:1]([O-])=[O:2].[Na+].[CH2:5]([O:7][C:8]([C:10]1[CH:11]=[C:12]([CH3:29])[C:13]2[O:19][C:18]3[C:20]([Cl:25])=[CH:21][C:22]([NH2:24])=[CH:23][C:17]=3[CH2:16][S:15](=[O:27])(=[O:26])[C:14]=2[CH:28]=1)=[O:9])[CH3:6].COC(C1C=C(C)C2OC3C(Cl)=CC(N)=CC=3CS(=O)(=O)C=2C=1)=O>C(O)=O>[CH2:5]([O:7][C:8]([C:10]1[CH:11]=[C:12]([CH3:29])[C:13]2[O:19][C:18]3[C:20]([Cl:25])=[CH:21][C:22]([NH:24][CH:1]=[O:2])=[CH:23][C:17]=3[CH2:16][S:15](=[O:27])(=[O:26])[C:14]=2[CH:28]=1)=[O:9])[CH3:6]
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Komponenten

5

Edukt 3

HCID 2723810Sodium FormateHCID 115596902-Amino-4-chloro-6-methyl-10,10-dioxo-10,11-dihydro-5-oxa-10lambda *6*-thia-dibenzo[a,d]cycloheptene-8-carboxylic acid methyl esterHCID 1317285262-Amino-4-chloro-6-methyl-10,10-dioxo-10,11-dihydro-5-oxa-10lambda*6*-thia-dibenzo[a,d]cycloheptene-8-carboxylic acid ethyl ester

Produkt 1

HCID 116829774-Chloro-2-formylamino-6-methyl-10,10-dioxo-10,11-dihydro-5-oxa-10lambda*6*-thia-dibenzo[a,d]cycloheptene-8-carboxylic acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 284Formic AcidLösungsmittel

Versuchsvorschrift

Sodium formate (0.075 g, 1.1 mmol) was added to a suspension of 2-amino-4-chloro-6-methyl-10,10-dioxo-10,11-dihydro-5-oxa-10lambda*6*-thia-dibenzo[a,d]cycloheptene-8-carboxylic acid ethyl ester (0.420 g, 1.1 mmol) [prepared by hydrolysis of compound of Example 1 and followed by esterification with ethanol/H2SO4] in formic acid (25 mL) and refluxed for 1.5 h. The reaction mixture was cooled and poured into ice water (100 mL). The solid precipitated was filtered, washed with water and dried. The crude product was purified by column chromatography (silica gel, 1% methanol in chloroform) to obtain the title compound. Yield: 0.21 g (47%); mp 202-204° C.; 1H NMR (DMSO-d6, 300 MHz): δ 1.31 (t, 3H, OCH2CH3), 2.64 (s, 3H, CH3), 4.31 (q, 2H, OCH2CH3), 5.25 (s, 2H, CH2, trans minor isomer), 5.33 (s, 2H, CH2, cis major isomer), 7.34 (d, 1H, Ar, trans minor isomer), 7.50 (d, 1H, Ar, trans minor isomer), 7.69 (d, 1H, Ar, cis major isomer), 7.86 (d, 1H, Ar, cis major isomer), 8.10 (s, 1H, Ar), 8.15 (s, 1H, Ar), 8.31 (s, 1H, CHO, cis major isomer), 8.80 (d, 1H, CHO, trans minor isomer), 10.43 (d, 1H, NH, trans minor isomer), 10.57 (s, 1H, NH, cis major isomer); MS: m/e (ES−) 408 (M−1); analysis: C18H16ClNO6S requires C, 52.75; H, 3.93; N, 3.42; Cl, 8.65; S, 7.82. found: C, 52.47; H, 3.86; N, 3.36; Cl, 8.81; S, 7.67%.

Aufarbeitung

  1. temperaturerefluxed for 1.5 h
  2. temperatureThe reaction mixture was cooled
  3. customThe solid precipitated
  4. filtrationwas filtered
  5. washwashed with water
  6. customdried
  7. customThe crude product was purified by column chromatography (silica gel, 1% methanol in chloroform)

Quellen und Nachweise

ORD-Eintrag
ord-ecfe4e14bbd046eca67803dc8bde3dd0
Quelldatensatz
uspto-grants-2011_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07964631B2

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