Diethylamine → N,N-diethyl-2-tert-butylbenzamide

HRID 1440534Notes

Reaction equation

HRID 1440534 reaction equation
[C:1]([C:5]1[CH:13]=[CH:12][CH:11]=[CH:10][C:6]=1[C:7]([OH:9])=O)([CH3:4])([CH3:3])[CH3:2].S(Cl)(Cl)=O.[CH2:18]([NH:20][CH2:21][CH3:22])[CH3:19]>C(Cl)Cl>[CH2:18]([N:20]([CH2:21][CH3:22])[C:7](=[O:9])[C:6]1[CH:10]=[CH:11][CH:12]=[CH:13][C:5]=1[C:1]([CH3:2])([CH3:3])[CH3:4])[CH3:19]

Participants

5

Reactant 3

HCID 8021DiethylamineHCID 24386Thionyl ChlorideHCID 136850tert-Butylbenzoic acid (mixed isomers)

Product 1

HCID 18630191N,N-diethyl-2-tert-butylbenzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2-tert-butylbenzoic acid (4.0 g, 22.5 mmol) in thionyl chloride (8.2 mL, 112 mmol) was stirred at RT for 2 h, then was concentrated three times from carbon tetrachloride to remove all traces of excess thionyl chloride. A solution of diethylamine (4.93 g, 67.4 mmol) in CH2Cl2 (10 mL) was added dropwise over 10 min to an ice water-cooled solution of the crude acid chloride in CH2Cl2 (35 mL). Ten min after addition was complete, the reaction was partitioned between ether and 10% HCl. The ether phase was then washed with sat aq NaHCO3, then was dried (MgSO4), and concentrated to afford a quantitative yield of N,N-diethyl-2-tert-butylbenzamide as an off-white solid. m.p. 38.5°-40.5° C.

Workup

  1. concentrationwas concentrated three times from carbon tetrachloride
  2. customto remove all traces of excess thionyl chloride
  3. additionTen min after addition
  4. customthe reaction was partitioned between ether and 10% HCl
  5. washThe ether phase was then washed with sat aq NaHCO3
  6. dry with materialwas dried (MgSO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-c0a4e4a71b0d4ab18a48bf4b0bb330a6
Source dataset
uspto-grants-1996_03
Patent number
US05498630

Reaction notes

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