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

HRID 716858

Reaction equation

HRID 716858 reaction equation
[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]

Participants

4

Reactant 2

HCID 6577Chloroacetyl chlorideHCID 74754-Nitroaniline

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-c799ec5f684d40ff855dd6407a630b64
Source dataset
uspto-grants-2015_11
Patent number
US09193687B2

Linked notes

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