1,2-Dichloroethane → HCID 20747587, compound

HRID 1663401Notes

Reaction equation

HRID 1663401 reaction equation
[C:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8](O)=[O:9])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[CH3:13][NH:14][CH3:15].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>CC#N>[C:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([N:14]([CH3:15])[CH3:13])=[O:9])=[CH:6][CH:5]=1)(=[O:3])[CH3:2]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 674DimethylamineHCID 114704-Acetylbenzoic AcidHCID 757711-HydroxybenzotriazoleHCID 81531Diisopropylethylamine

Product 1

HCID 20747587HCID 20747587, compoundYield 84.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 4-acetylbenzoic acid (10.0 g, 60.9 mmol), 40% aqueous solution of dimethylamine (8.24 g, 73.1 mmol), EDC (14.0 g, 73.1 mmol), HOBT (11.2 g, 73.1 mmol) and DIEA (21.3 mL, 122 mmol) in CH3CN (150 mL) was stirred at room temperature for 15 h and concentrated. The residue was dissolved in ethyl acetate (600 mL), washed with water (2×80 mL), brine (80 mL), dried (MgSO4) and concentrated to provide 4-acetyl-N,N-dimethylbenzamide (9.80 g, 84%). MS (E+) m/z: 191 (M+H); HPLC retention time: 0.88 min (Analytical HPLC Method F).

Workup

  1. concentrationconcentrated
  2. dissolutionThe residue was dissolved in ethyl acetate (600 mL)
  3. washwashed with water (2×80 mL), brine (80 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-b5b603fc6a2a4d2999ec3b807a01474a
Source dataset
uspto-grants-2011_10
Patent number
US08034940B2

Reaction notes

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