Triethylamine → HCID 19429435, compound

HRID 1078382Notes

Reaction equation

HRID 1078382 reaction equation
[Cl:1][CH2:2][C:3]([CH3:8])([CH3:7])[C:4](Cl)=[O:5].[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([CH:16]([NH2:18])[CH3:17])=[CH:12][CH:11]=1.C(N(CC)CC)C>ClCCl>[Cl:1][CH2:2][C:3]([CH3:8])([CH3:7])[C:4]([NH:18][CH:16]([C:13]1[CH:14]=[CH:15][C:10]([Cl:9])=[CH:11][CH:12]=1)[CH3:17])=[O:5]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 613453-Chloro-2,2-dimethylpropanoyl chlorideHCID 978031-(4-Chlorophenyl)ethylamine

Product 1

HCID 19429435HCID 19429435, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 3-chloro-2,2-dimethylpropionyl chloride (7.0 g) in dichloromethane (50 ml) was added dropwise to a stirred solution of 1-(4-chlorophenyl)ethylamine (7.0 g) and triethylamine (6.3 ml) in dichloromethane (100 ml) at 0°-5° C. under nitrogen. After the addition, the mixture was stirred at 0° C. for 0.5 hours and then stirred at ambient temperature for 2 hours. The mixture was washed with 5M hydrochloric acid and then with water. The mixture was dried and evaporated. The residue was recrystallised from petroleum ether (b.p. 60°-80° C.) to give 3-chloro-N-[1-(4-chlorophenyl)ethyl]-2,2-dimethylpropionamide, m.p. 95°-96° C.

Workup

  1. additionAfter the addition
  2. stirringstirred at ambient temperature for 2 hours
  3. washThe mixture was washed with 5M hydrochloric acid
  4. customThe mixture was dried
  5. customevaporated
  6. customThe residue was recrystallised from petroleum ether (b.p. 60°-80° C.)

Sources & evidence

ORD record
ord-a61d29c8c2f846b6b2a971acdf14741c
Source dataset
uspto-grants-1996_08
Patent number
US05547972

Reaction notes

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