Dimethylformamide → 3-Nitrobenzeneacetyl chloride

HRID 1422595Notes

Reaction equation

HRID 1422595 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH2:10][C:11]([OH:13])=O)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].S(Cl)([Cl:16])=O.CN(C=O)C>C1(C)C=CC=CC=1>[N+:1]([C:4]1[CH:5]=[C:6]([CH2:10][C:11]([Cl:16])=[O:13])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 158763-Nitrophenylacetic acidHCID 24386Thionyl Chloride

Product 1

HCID 5232253-Nitrobenzeneacetyl chlorideYield 98.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of commercially available 2-(3-nitrophenyl)acetic acid [CAS no. 1877-73-2] (25.8 g, 142 mmol, Eq: 1.00) and thionyl chloride (25.4 g, 15.5 ml, 214 mmol, Eq: 1.5) in toluene (141 ml) and DMF (208 mg, 221 μl, 2.85 mmol, Eq: 0.02) was stirred at 80° C. for 2 h. The hot solution was filtered through a Sartorius filter, the filtrate was evaporated and dried in HV to give the 2-(3-nitrophenyl)acetyl chloride (28.12 g, 141 mmol, 98.9% yield) as a yellow solid, which was used without further purification.

Workup

  1. filtrationThe hot solution was filtered through a Sartorius
  2. filtrationfilter
  3. customthe filtrate was evaporated
  4. customdried in HV

Sources & evidence

ORD record
ord-ab7f7cfc6b84419e8f8706494544f835
Source dataset
uspto-grants-2015_01
Patent number
US08927535B2

Reaction notes

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