Chloroacetyl chloride → Acetanilide, 2-chloro-4'-nitro-

HRID 716858Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 716858
[N+:1]([C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[CH:6][CH:5]=1)([O-:3])=[O:2].[Cl:11][CH2:12][C:13](Cl)=[O:14]>C1COCC1>[Cl:11][CH2:12][C:13]([NH:8][C:7]1[CH:9]=[CH:10][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1)=[O:14]

Komponenten

4

Edukt 2

HCID 6577Chloroacetyl chlorideHCID 74754-Nitroaniline

Produkt 1

HCID 140220Acetanilide, 2-chloro-4'-nitro-

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a solution of 4-nitroaniline 37b (6.9 g, 50 mmol) in THF (50 mL) was added dropwise a solution of chloroacetyl chloride (100 mmol) in dry THF (50 mL) at room temperature. The reaction mixture was stirred for additional 40-45 minutes and then evaporated in vacuo to dryness. The solid residue was triturated with saturated NaHCO3 solution (aqueous) and then collected by filtration. The solid product was washed with water, followed by hexane, and dried to give 2-chloro-N-(4-nitrophenyl)acetamide, 10.02 g (94%); mp 182-183° C. (Lit. 181-183° C.58). 1H NMR (DMSO-d6) δ: 4.34 (2H, s, CH2), 7.83-7.85 (2H, d, J=9.1 Hz, Ar—H), 8.23-8.26 (2H, d, J=9.1 Hz, Ar—H), 10.88 (1H, brs, NH).

Aufarbeitung

  1. customevaporated in vacuo to dryness
  2. customThe solid residue was triturated with saturated NaHCO3 solution (aqueous)
  3. filtrationcollected by filtration
  4. washThe solid product was washed with water
  5. customdried

Quellen und Nachweise

ORD-Eintrag
ord-c799ec5f684d40ff855dd6407a630b64
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09193687B2

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