Toluene → Benzeneacetamide

HRID 2292713Notes

Reaction equation

HRID 2292713 reaction equation
CN(C[N:5]([CH3:7])C)C.C(Cl)(=[O:10])C.[CH3:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>>[C:13]1([CH2:12][C:7]([NH2:5])=[O:10])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 3

HCID 1140Toluene3×HCID 5829N,N,N',N'-TetramethylmethanediamineHCID 6367Acetyl chloride

Product 1

HCID 7680Benzeneacetamide

Conditions

Temperature
20 °C

Procedure

To a stirred solution of 3.37 parts of N,N,N',N'-tetramethyldiaminomethane in 44 parts of methylbenzene was added dropwise a solution of 2.59 parts of acetylchloride in 26 parts of methylbenzene during 30 minutes at 20°-25° C. under nitrogen atmosphere. Upon completion, the reaction mixture was further stirred for 20 minutes. 10.21 Parts of compound 15 and 78 parts of methylbenzene were added to the previous mixture and stirred for 5 hours at 80° C. The reaction mixture was allowed to cool to 20° C., the precipitated product was filtered off and dried in vacuo at 40° C., yielding 11.66 parts (97.8%) of N-[(dimethylamino)methyl]2,6-dichloro-α-[2-nitrophenyl)amino]benzeneacetamide.

Workup

  1. stirringstirred for 5 hours at 80° C
  2. filtrationthe precipitated product was filtered off
  3. customdried in vacuo at 40° C.

Sources & evidence

ORD record
ord-6b2b36fb35ae4621bb2b5519dcf788f1
Source dataset
uspto-grants-1997_11
Patent number
US05684049

Reaction notes

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