Ethyl orthoformate → HCID 58503275, compound

HRID 1895862Notes

Reaction equation

HRID 1895862 reaction equation
[Cl:1][C:2]1[CH:30]=[CH:29][CH:28]=[CH:27][C:3]=1[CH2:4][N:5]1[C:9]([NH2:10])=[C:8]([C:11]2[C:15](=[NH:16])[N:14]([CH2:17][C:18]3[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=3)[C:13](=[O:26])[N:12]=2)[N:7]=[CH:6]1.[CH:31](OCC)(OCC)OCC>CC#N.S(=O)(=O)(O)O>[CH3:25][O:24][C:21]1[CH:22]=[CH:23][C:18]([CH2:17][N:14]2[C:15]3=[N:16][CH:31]=[N:10][C:9]4[N:5]([CH2:4][C:3]5[CH:27]=[CH:28][CH:29]=[CH:30][C:2]=5[Cl:1])[CH:6]=[N:7][C:8]=4[C:11]3=[N:12][C:13]2=[O:26])=[CH:19][CH:20]=1

Participants

5

Reactant 2

HCID 31214Ethyl orthoformateHCID 58503307HCID 58503307, compound

Product 1

HCID 58503275HCID 58503275, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 6342AcetonitrileSolvent

Procedure

To a suspension of 20 (3.5 g, 8.29 mmol, 1 equiv) in MeCN (30 mL), triethyl orthoformate (6.2 mL, 41.46 mmol, 5 equiv) was added followed by 4 drops of sulfuric acid. The reaction mixture was heated at reflux for 1.5 h until starting material was disappeared (TLC). The precipitated product was filtered, washed with diethyl ether and dried under vacuum to afford the pure product 21 (RK-12) as a pale yellow solid (3 g, 85%). IR: 1745 (C═O str.), 1621, 1586, 1248, 1171, 759 (C—Cl str.) cm−1. 1H NMR (400 MHz, d6-DMSO): δ=3.71 (s, 3H, OCH3), 5.09 (s, 2H, CH2), 5.68 (s, 2H, CH2), 6.86 (d, J=8.7 Hz, 2H, Ar—H), 6.98-6.99 (m, 1H, Ar—H), 7.25-7.27 (m, 1H, Ar—H), 7.30 (d, J=8.7 Hz, 2H, Ar—H), 7.34-7.38 (m, 1H, Ar—H), 7.53-7.55 (m, 1H, Ar—H), 8.70 (s, 1H, Ar—C═N—H), 8.86 (s, 1H, Imid-H). MS (ESI+ve) m/z: 433.2 (M+H)+, 455.1 (M+Na)+.

Workup

  1. additionwas added
  2. temperatureThe reaction mixture was heated
  3. temperatureat reflux for 1.5 h
  4. filtrationThe precipitated product was filtered
  5. washwashed with diethyl ether
  6. customdried under vacuum

Sources & evidence

ORD record
ord-5afe2691bc4c44d683a58bfdba966f72
Source dataset
uspto-grants-2013_08
Patent number
US08518901B2

Reaction notes

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