Triethylamine → HCID 22200564, compound

HRID 1014233Notes

Reaction equation

HRID 1014233 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].C1COCC1.ClCCCl.C(N(CC)CC)C.Cl.[CH3:29][N:30]([CH3:35])[CH2:31][C:32](Cl)=[O:33]>CN(C1C=CN=CC=1)C.ClCCl>[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:32](=[O:33])[CH2:31][N:30]([CH3:35])[CH3:29])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 124774-Chloro-3-nitroanilineHCID 139949912-(Dimethylamino)acetyl chloride hydrochlorideHCID 21493386Dce thf

Product 1

HCID 22200564HCID 22200564, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of 4-chloro-3-nitroaniline (1.0 g, 5.81 mmol) in 1:1 THF/DCE (200 mL) was added triethylamine (3.53 g, 34.9 mmol, Aldrich), 2-dimethylaminoacetyl chloride hydrochloride (1.82 g, 11.6 mmol, Alfa Aesar), and catalytic DMAP (Aldrich). After heating overnight at 65° C., the crude reaction mixture was diluted with dichloromethane (300 mL), washed with saturated NaHCO3 (50 mL), evaporated, and purified by column chromatography (dichloromethane to 5% methanol/dichloromethane) to provide N1-(4-chloro-3-nitrophenyl)-N2,N2-dimethylglycinamide (1.0 g, 67%) as a brown solid. ESIMS (M+H)+=258.

Workup

  1. customthe crude reaction mixture
  2. washwashed with saturated NaHCO3 (50 mL)
  3. customevaporated
  4. custompurified by column chromatography (dichloromethane to 5% methanol/dichloromethane)

Sources & evidence

ORD record
ord-4eb89910d6a7436dba26eb7988e9f323
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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