Acetic Acid → HCID 57961921, compound

HRID 541946Notes

Reaction equation

HRID 541946 reaction equation
FC(F)(F)C(O)=O.FC(F)(F)C(O)=O.[Cl:15][C:16]1[N:21]=[C:20]([NH:22][C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([NH:29][CH2:30][CH2:31][O:32][C:33]3[CH:38]=[CH:37][CH:36]=[C:35]([N+:39]([O-])=O)[CH:34]=3)[CH:24]=2)[C:19]([Cl:42])=[CH:18][N:17]=1.C(O)(=O)C.O>CO.[Fe]>[NH2:39][C:35]1[CH:34]=[C:33]([CH:38]=[CH:37][CH:36]=1)[O:32][CH2:31][CH2:30][NH:29][C:25]1[CH:26]=[CH:27][CH:28]=[C:23]([NH:22][C:20]2[C:19]([Cl:42])=[CH:18][N:17]=[C:16]([Cl:15])[N:21]=2)[CH:24]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 962WaterHCID 86636295HCID 86636295, compound

Product 1

HCID 57961921HCID 57961921, compoundYield 107.6%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 887MethanolSolvent2×

Conditions

Temperature
20 °C

Procedure

A solution of N-(2,5-dichloropyrimidin-4-yl)-N′-[2-(3-nitrophenoxy)ethyl]benzene-1,3-diamine bis(trifluoroacetate) (100 mg, 0.15 mmol) in methanol (0.63 mL) was treated with acetic acid (0.25 mL, 4.4 mmol), water (0.13 mL, 7.0 mmol), and iron (43 mg, 0.77 mmol) and stirred at 20° C. for 16 h. The reaction mixture was diluted with methanol and treated with celite. The suspension was filtered over a pad of celite and washed with methanol. The filtrate was concentrated to give the desired product (63 mg, 94%) as a crude residue that was used without further purification.

Workup

  1. additiontreated with celite
  2. filtrationThe suspension was filtered over a pad of celite
  3. washwashed with methanol
  4. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-1cccfe3839f8481ba3bc5f7d03e43d6c
Source dataset
uspto-grants-2014_10
Patent number
US08871753B2

Reaction notes

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