Aniline → Chloroacetanilide

HRID 1053552Notes

Reaction equation

HRID 1053552 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:8][CH2:9][C:10](Cl)=[O:11]>N1C=CC=CC=1.C(Cl)Cl>[Cl:8][CH2:9][C:10]([NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:11]

Participants

5

Reactant 2

HCID 6115AnilineHCID 6577Chloroacetyl chloride

Product 1

HCID 11485ChloroacetanilideYield 91.1%

Reagents, catalysts & solvents 2

HCID 1049PyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of aniline (1 mL, 11 mmol) and CH2Cl2 (150 mL), pyridine (886 mL, 1 mmol) was added. Then 2-chloroacetyl chloride (872 mL, 11 mmol) was added dropwise over 10 min. After the addition was complete, the mixture was reacted at room temperature for 2 hours. The reaction was then quenched with water (100 mL), the layers were separated and the aqueous layer was extracted with CH2Cl2 (2×50 mL). The combined organic layer was washed water, brine, and dried over Na2SO4. The solvent was evaporated to give a colorless solid (1.7 g, 91% yield). The crude product was directly used for next step. 1H NMR (CDCl3, 400 MHz) δ 8.25 (br s., 1H), 7.57 (d, J=7.6 Hz, 2H), 7.39 (t, J=7.6 Hz, 2H), 7.20 (t, J=7.4 Hz, 1H), 4.22 (s, 2H).

Workup

  1. additionAfter the addition
  2. customthe mixture was reacted at room temperature for 2 hours
  3. customThe reaction was then quenched with water (100 mL)
  4. customthe layers were separated
  5. extractionthe aqueous layer was extracted with CH2Cl2 (2×50 mL)
  6. washThe combined organic layer was washed water, brine
  7. dry with materialdried over Na2SO4
  8. customThe solvent was evaporated

Sources & evidence

ORD record
ord-78f43fd29e9e40d4942db8d4b8b24b5f
Source dataset
uspto-grants-2016_07
Patent number
US09394233B2

Reaction notes

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