Water → 2-Chloro-N-(2,6-diisopropylphenyl)acetamide

HRID 2396120Notes

Reaction equation

HRID 2396120 reaction equation
[CH:1]([C:4]1[CH:10]=[CH:9][CH:8]=[C:7]([CH:11]([CH3:13])[CH3:12])[C:5]=1[NH2:6])([CH3:3])[CH3:2].C(N(CC)CC)C.[Cl:21][CH2:22][C:23](Cl)=[O:24].O>O1CCCC1>[CH:11]([C:7]1[CH:8]=[CH:9][CH:10]=[C:4]([CH:1]([CH3:3])[CH3:2])[C:5]=1[NH:6][C:23](=[O:24])[CH2:22][Cl:21])([CH3:13])[CH3:12]

Participants

6

Reactant 4

HCID 962WaterHCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 32484Diisopropylaniline

Product 1

HCID 23637742-Chloro-N-(2,6-diisopropylphenyl)acetamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Part A. A solution of 2,6-diisopropylaniline (10.0 mL, 53.0 mmol) and triethylamine (10.0 mL, 71.7 mmol) in tetrahydrofuran (100 mL) was cooled to 0° C., and treated dropwise with a solution of chloroacetyl chloride (5.00 mL, 62.8 mmol) in tetrahydrofuran (20 mL). After being stirred for 10 hours, the solution was poured into water (200 mL) and extracted with methylene chloride (2×200 mL). The extracts were combined, dried over anhydrous magnesium sulfate, filtered and evaporated to afford the product, N-(2,6-diisopropylphenyl)-2-chloroacetamide, as a solid. The solid was purified by trituration in boiling ether, filtration and drying; mp 157°-158° C. (10.7 g, 42.0 mmol, 79%). 1HNMR (CDCl3): δ 7.81 (1H, br s); 7.32 (1H, t, J=8.1 Hz); 7.19 (2H, d, J=8 Hz); 4.26 (2H, s); 3.02 (2H, heptet, J=6.6 Hz); 1.21 (12H, d, J=6.6 Hz). Mass spectrum (NH3 -CI/DDIP): m/z 271 (100%); 256 (11%); 255 (6%); 254 (30%); 219 (1%).

Workup

  1. extractionextracted with methylene chloride (2×200 mL)
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-a4650331da6146e6beb08f2682d70279
Source dataset
uspto-grants-1996_02
Patent number
US05491152

Reaction notes

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