Acetyl chloride → HCID 18698654, compound

HRID 2290032Notes

Reaction equation

HRID 2290032 reaction equation
[N+:1]([C:4]1[CH:13]=[CH:12][C:7]([NH:8][CH2:9][CH2:10][OH:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].C(N(CC)CC)C.[C:21](Cl)(=[O:23])[CH3:22]>ClCCl.CN(C)C1C=CN=CC=1.C(OCC)C>[C:21]([O:11][CH2:10][CH2:9][NH:8][C:7]1[CH:12]=[CH:13][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1)(=[O:23])[CH3:22]

Participants

7

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 2661542-[(4-nitrophenyl)amino]ethanol

Product 1

HCID 18698654HCID 18698654, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a flask containing 2-(4-nitroanilino)-1-ethanol (0.91 g) in dichloromethane (25 mL) at 0° C. is added triethylamine (1.8 mL), acetyl chloride (0.85 mL) and 4-dimethylaminopyridine (0.06 g). The reaction mixture is allowed to warm to room temperature over 3 hours. The reaction mixture is diluted with diethyl ether, washed with saturated aqueous sodium bicarbonate, brine, dried over sodium sulfate and concentrated under reduced pressure. The residue is chromatographed on silica eluting with 50% ethyl acetate in heptane. The product-containing fractions are evaporated to give 0.61 g of 2-(4-Nitroanilino)ethyl acetate as a yellow solid To a Parr bottle containing 2-(4-nitroanilino)ethyl acetate (0.61 g) and ethyl acetate (10 mL) is added 10% palladium on carbon (0.05 g). The reaction mixture is shaken for 2 hours under 50 psi of hydrogen gas. The reaction mixture is filtered through Celite with ethyl acetate washes. The filtrate is concentrated under reduced pressure. The residue is treated with diethyl ethoxymethylenemalonate (0.60 mL) and heated to 135° C. under a flow of argon gas. After 1 hour the reaction is cooled to room temperature, adsorbed onto silica gel, and chromatographed on silica eluting with 60% to 80% ethyl acetate in heptane. The product-containing fractions are evaporated to give 0.45 g diethyl 2-[(4-{[2-(acetyloxy)ethyl]amino}-anilino)methylene]malonate as a yellow solid.

Workup

  1. washwashed with saturated aqueous sodium bicarbonate, brine
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue is chromatographed on silica eluting with 50% ethyl acetate in heptane
  5. customThe product-containing fractions are evaporated

Sources & evidence

ORD record
ord-778625c280d845f0aa6614cda5a2dba3
Source dataset
uspto-grants-2000_07
Patent number
US06093732

Reaction notes

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