Ethanol → HCID 57967261, compound

HRID 1401341Notes

Reaction equation

HRID 1401341 reaction equation
[F:1][C:2]1[CH:36]=[C:35]([N+:37]([O-])=O)[CH:34]=[CH:33][C:3]=1[O:4][C:5]1[C:10]2[S:11][C:12]([C:14]3[N:19]=[C:18]([CH2:20][N:21]([CH2:29][CH2:30][O:31][CH3:32])[C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[CH:17]=[CH:16][CH:15]=3)=[CH:13][C:9]=2C=[CH:7][CH:6]=1.[NH4+:40].[Cl-].CCO>[Fe].O>[NH2:37][C:35]1[CH:34]=[CH:33][C:3]([O:4][C:5]2[CH:6]=[CH:7][N:40]=[C:9]3[CH:13]=[C:12]([C:14]4[N:19]=[C:18]([CH2:20][N:21]([CH2:29][CH2:30][O:31][CH3:32])[C:22](=[O:28])[O:23][C:24]([CH3:25])([CH3:27])[CH3:26])[CH:17]=[CH:16][CH:15]=4)[S:11][C:10]=23)=[C:2]([F:1])[CH:36]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 25517Ammonium ChlorideHCID 86636116HCID 86636116, compound

Product 1

HCID 57967261HCID 57967261, compoundYield 103.8%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Procedure

A solution of 58 (1 g, 1.81 mmol) and NH4Cl (97 mg, 1.8 mmol) in a 2:1 mixture of EtOH and water (30 mL) was treated with iron powder (605 mg, 10.8 mmol) and stirred at reflux for 1 hour. The reaction mixture was then filtered through a celite pad and concentrated yielding title compound 59 (980 mg, 100% yield) that was used in the next step (scheme 18) without further purification. MS (m/z): 525.2 (M+1).

Workup

  1. temperatureat reflux for 1 hour
  2. filtrationThe reaction mixture was then filtered through a celite pad
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-d648351e52ca4bd28bd355affd398e7e
Source dataset
uspto-grants-2014_12
Patent number
US08907091B2

Reaction notes

Loading…