Acetyl chloride → Acetamide, N-(2,6-dichlorophenyl)- (9CI)

HRID 1493496Notes

Reaction equation

HRID 1493496 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([Cl:9])[C:3]=1[NH2:4].[C:10](Cl)(=[O:12])[CH3:11]>C(O)(=O)C>[CH3:11][C:10]([NH:4][C:3]1[C:2]([Cl:1])=[CH:8][CH:7]=[CH:6][C:5]=1[Cl:9])=[O:12]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 118462,6-Dichloroaniline

Product 1

HCID 28698Acetamide, N-(2,6-dichlorophenyl)- (9CI)

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
90 °C

Procedure

To a mechanically stirred solution of 2,6-dichloroaniline (76 g, 0.047 mol) in 60 mL of glacial acetic acid is added dropwise acetyl chloride (36 mL, 0.5 mol). After the addition is complete, the reaction mixture is heated at 90° C. for 20 minutes. The solution is poured into ice water (500 mL), forming a white precipitate. The solids are filtered, washed with water and dried to give the product (91.8 g, 96%, white solid, m.p. 179°-180° C., lit. m.p. 180°-181° C. from glacial acetic acid).

Workup

  1. additionAfter the addition
  2. customforming a white precipitate
  3. filtrationThe solids are filtered
  4. washwashed with water
  5. customdried
  6. customto give the product (91.8 g, 96%, white solid, m.p. 179°-180° C., lit. m.p. 180°-181° C. from glacial acetic acid)

Sources & evidence

ORD record
ord-98ed9fce6a324ceab8053d2b51e9f9a4
Source dataset
uspto-grants-1991_06
Patent number
US05021576

Reaction notes

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