3,4-Dichloroaniline → 2,3-Dichloro-N-[(3,4-dichlorophenyl)carbamoyl]propanamide

HRID 866775Notes

Reaction equation

HRID 866775 reaction equation
[Cl:1][CH:2]([CH2:8][Cl:9])[C:3]([N:5]=[C:6]=[O:7])=[O:4].[Cl:10][C:11]1[CH:12]=[C:13]([CH:15]=[CH:16][C:17]=1[Cl:18])[NH2:14]>C1C=CC=CC=1>[Cl:10][C:11]1[CH:12]=[C:13]([NH:14][C:6]([NH:5][C:3](=[O:4])[CH:2]([Cl:1])[CH2:8][Cl:9])=[O:7])[CH:15]=[CH:16][C:17]=1[Cl:18]

Participants

4

Reactant 2

HCID 72573,4-DichloroanilineHCID 203185352,3-Dichloropropanoyl isocyanate

Product 1

HCID 203185612,3-Dichloro-N-[(3,4-dichlorophenyl)carbamoyl]propanamideYield 76%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Conditions

Temperature
20 °C

Procedure

A solution of 17.0 g (0.1 mole) of 2,3-dichloropropionyl isocyanate in 50 ml of wash benzine was added dropwise to a solution of 16.0 g (0.1 mole) of 3,4-dichloroaniline in 150 ml of dry benzene at 0° to 5° C, while cooling. In the course thereof, the reaction product crystallized out. The mixture was stirred for a further hour at 20° C and was filtered, and the product was washed with petroleum ether and dried. 25 g of N-(3,4-dichlorophenyl)-N'-(2,3-dichloropropionyl)-urea of melting point 145° to 148° C, with decomposition, were obtained. The yield was 76% of theory.

Workup

  1. temperaturewhile cooling
  2. customIn the course thereof, the reaction product crystallized out
  3. filtrationwas filtered
  4. washthe product was washed with petroleum ether
  5. customdried

Sources & evidence

ORD record
ord-e0465ca36bea474caabec70f7cd52b7b
Source dataset
uspto-grants-1978_07
Patent number
US04101575

Reaction notes

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