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

HRID 356344

Reaction equation

HRID 356344 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-butyl-benzamide 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-22cd3e9d2c49474ea4407d646d8695ec
Source dataset
uspto-grants-1998_11
Patent number
US05834447

Linked notes

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