Ethanol → HCID 57967261, compound

HRID 1475569Notes

Reaction equation

HRID 1475569 reaction equation
[C:1]([O:5][C:6](=[O:39])[N:7]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([C:19]2[S:23][C:22]3[C:24]([O:28][C:29]4[CH:34]=[CH:33][C:32]([N+:35]([O-])=O)=[CH:31][C:30]=4[F:38])=[CH:25][CH:26]=C[C:21]=3[CH:20]=2)[N:14]=1)[CH2:8][CH2:9][O:10][CH3:11])([CH3:4])([CH3:3])[CH3:2].[NH4+:40].[Cl-].CCO>[Fe].O>[C:1]([O:5][C:6](=[O:39])[N:7]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([C:19]2[S:23][C:22]3[C:21](=[N:40][CH:26]=[CH:25][C:24]=3[O:28][C:29]3[CH:34]=[CH:33][C:32]([NH2:35])=[CH:31][C:30]=3[F:38])[CH:20]=2)[N:14]=1)[CH2:8][CH2:9][O:10][CH3:11])([CH3:4])([CH3:3])[CH3:2]

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-f592a57b6c7c4cca9abf2c94cce8b33b
Source dataset
uspto-grants-2015_04
Patent number
US09018378B2

Reaction notes

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