Hydrochloric Acid → 2,6,N'-trimethyl-N'-(4-trifluoromethyl-benzyl)-benzene-1,4-diamine

HRID 1820121Notes

Reaction equation

HRID 1820121 reaction equation
Cl.[CH3:2][C:3]1[CH:8]=[C:7]([N:9]([CH3:21])[CH2:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=2)[CH:6]=[C:5]([CH3:22])[C:4]=1[NH:23]C(=O)C.[OH-].[K+]>>[CH3:2][C:3]1[CH:8]=[C:7]([N:9]([CH3:21])[CH2:10][C:11]2[CH:12]=[CH:13][C:14]([C:17]([F:18])([F:19])[F:20])=[CH:15][CH:16]=2)[CH:6]=[C:5]([CH3:22])[C:4]=1[NH2:23]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 11638852N-{2,6-Dimethyl-4-[methyl-(4-trifluoromethyl-benzyl)-amino]-phenyl}-acetamide

Product 1

HCID 685154092,6,N'-trimethyl-N'-(4-trifluoromethyl-benzyl)-benzene-1,4-diamineYield 57%

Conditions

Temperature
130 °C

Procedure

Concentrated aqueous hydrochloric acid (2 mL) was added to N-{2,6-dimethyl-4-[methyl-(4-trifluoromethyl-benzyl)-amino]-phenyl}-acetamide (0.20 g) and heated to 130° C. for 80 minutes in a sealed microwave process vial. The crude mixture was poured onto solid potassium hydroxide (2 g) mixed with ice. The product was extracted with 1,2-dichloroethane (100 mL), and the organic phase was filtered through solid sodium carbonate (5 g), dried over magnesium sulfate and concentrated in vacuo to furnish 0.10 g (57% yield) of the title compound as a pale brown oil. LC-MS (m/z) 309 (MH+); tR=2.11, (UV, ELSD) 99%, 98%. 1H NMR (500 MHz, DMSO-d6): 2.03 (s, 6H), 2.76 (s, 3H), 3.94 (b, 2H), 4.41 (s, 2H), 6.39 (s, 2H), 7.42 (d, 2H), 7.65 (d, 2H).

Workup

  1. additionmixed with ice
  2. extractionThe product was extracted with 1,2-dichloroethane (100 mL)
  3. filtrationthe organic phase was filtered through solid sodium carbonate (5 g)
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a2b0a5aa4f494c098f6b2d86d5fee9ff
Source dataset
uspto-grants-2009_10
Patent number
US07601870B2

Reaction notes

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