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Chloroacetyl chloride → 2-chloro-N-[4-chloro-3-(trifluoromethyl)phenyl]acetamide

HRID 1809152
Notes
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Reaction equation

HRID 1809152 reaction equation
[Cl:1][CH2:2][C:3](Cl)=[O:4].[NH2:6][C:7]1[CH:8]=[CH:9][C:10]([Cl:17])=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:12]=1.C(N(CC)CC)C>C(Cl)Cl>[Cl:1][CH2:2][C:3]([NH:6][C:7]1[CH:8]=[CH:9][C:10]([Cl:17])=[C:11]([C:13]([F:16])([F:14])[F:15])[CH:12]=1)=[O:4]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 675744-Chloro-3-(trifluoromethyl)aniline

Product 1

HCID 23077292-chloro-N-[4-chloro-3-(trifluoromethyl)phenyl]acetamideYield 84.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a round bottom flask was added chloroacetyl chloride (2.0 mL, 25.0 mmol, 1.0 eq.) and CH2Cl2 (100 mL). The solution was cooled to 0° C. before a mixture of 5-amino-2-chloro-benzotrifluoride (4.88 g, 25.0 mmol, 1.0 eq.) and triethyl amine (3.56 mL, 27.5 mmol, 1.1 eq.) in CH2Cl2 (5.0 mL) was added dropwise. The reaction was then stirred at 0° C. for 1.5 h before quenching with H2O (50 mL). The organic layer was then separated, washed with brine, and dried with Na2SO4. Concentration via rotary evaporation gave acetamide 21 as a yellow solid (5.72 g, 84.7% yield). 1H-NMR, Varian 400 MHz (DMSO-d6) δ 10.79 (br s, 1H), 8.20 (d, 1H), 7.87 (dd, 1H), 7.75 (d, 1H), 4.36 (s, 2H) ppm.

Workup

  1. additionwas added dropwise
  2. custombefore quenching with H2O (50 mL)
  3. customThe organic layer was then separated
  4. washwashed with brine
  5. dry with materialdried with Na2SO4
  6. concentrationConcentration
  7. customvia rotary evaporation

Sources & evidence

ORD record
ord-827dbbb3ee154d9e9d1c7e5a8ea9fd62
Source dataset
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08362017B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes