Acetic Acid → HCID 19063666, compound

HRID 482337Notes

Reaction equation

HRID 482337 reaction equation
[CH3:1][C:2]([CH3:4])=O.[CH3:5][N:6]([CH3:14])[C:7]1[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][CH:8]=1.C(O)(=O)C.C([BH3-])#N.[Na+].C1COCC1>CO>[CH:2]([NH:13][C:10]1[CH:11]=[CH:12][C:7]([N:6]([CH3:14])[CH3:5])=[CH:8][CH:9]=1)([CH3:4])[CH3:1]

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 180AcetoneHCID 7472N,N-dimethyl-p-phenylenediamineHCID 8028TetrahydrofuranHCID 5003444Sodium cyanoborohydride

Product 1

HCID 19063666HCID 19063666, compoundYield 106.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Acetone (30 mL, 408 mmol) is added to a mixture of N',N'-dimethyl-benzene-1,4-diamine (27.2 g, 200 mmol), acetic acid (glacial, 13.8 mL, 241 mmol), methanol (500 mL), and sodium cyanoborohydride in THF (1M, 440 mL, 440 mmol) and allowed to stir overnight under nitrogen. After concentrating in vacuo to a residue, the reaction mixture is partitioned between ethyl acetate and aqueous sodium carbonate. The layers are separated and the aqueous layer is extracted twice with ethyl acetate. The organic layers are combined, extracted with saturated brine, dried over anhydrous potassium carbonate, and concentrated in vacuo to afford the title compound as an oil (38.0 g, 213 mmol) of sufficient purity for the next step. 1H NMR (300 MHz, CDCl3) δ=1.18 (d, J=6.28 Hz, 6H); 2.82 (s, 6H); 3.04 (b, 1H), 3.47-3.59 (m, 1H); 6.59 (d, J=9.0 Hz, 2H); 6.73 (d, J=9.0 Hz, 2H). TLC Rf -0.3 (20:80 ethyl acetate: n-hexane).

Workup

  1. concentrationAfter concentrating in vacuo to a residue
  2. customthe reaction mixture is partitioned between ethyl acetate and aqueous sodium carbonate
  3. customThe layers are separated
  4. extractionthe aqueous layer is extracted twice with ethyl acetate
  5. extractionextracted with saturated brine
  6. dry with materialdried over anhydrous potassium carbonate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e3a913ed47774254a558055737686030
Source dataset
uspto-grants-1998_08
Patent number
US05795887

Reaction notes

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