Water → HCID 18949210, compound

HRID 1768674Notes

Reaction equation

HRID 1768674 reaction equation
NCC[C:4]1[CH:12]=[CH:11][C:7]([C:8]([O-:10])=[O:9])=[CH:6][CH:5]=1.C([N:15](CC)CC)C.[C:20]([C:26]1[CH:34]=[CH:33][C:29]([C:30](Cl)=[O:31])=[CH:28][CH:27]=1)(=[O:25])[C:21]([CH3:24])([CH3:23])[CH3:22].O.CCO[CH2:39][CH3:40]>>[CH3:22][C:21]([CH3:24])([CH3:23])[C:20]([C:26]1[CH:34]=[CH:33][C:29]([C:30]([NH:15][C:4]2[CH:5]=[CH:6][C:7]([C:8]([O:10][CH2:39][CH3:40])=[O:9])=[CH:11][CH:12]=2)=[O:31])=[CH:28][CH:27]=1)=[O:25]

Participants

6

Reactant 5

HCID 962WaterHCID 3283Diethyl Ether2×HCID 8471TriethylamineHCID 11806342Benzoyl chloride, 4-(2,2-dimethyl-1-oxopropyl)-HCID 131718822HCID 131718822, compound

Product 1

HCID 18949210HCID 18949210, compound

Procedure

A mixture of 247.5 grams (1.5 moles) of p-aminoethylbenzoate and 171.7 grams (1.7 moles) of triethylamine in 6 liters of ether is cooled to -30°; and 336 grams (1.5 moles) p-pivaloyl benzoyl chloride in 1.5 liters of ether is added dropwise while maintaining the temperature during addition between -30° and -50° C. At the end of the addition, the reaction mixture is allowed to warm to room temperature and is stirred overnight. One liter of water is then added to the mixture, and the stirring is continued for 2 hours at room temperature. The mixture is filtered and the solid obtained is washed with water and cold ether to yield the title product (M.P 157°-159° C.).

Workup

  1. temperatureis cooled to -30°
  2. temperaturewhile maintaining the temperature
  3. additionduring addition between -30° and -50° C
  4. additionAt the end of the addition
  5. waitthe stirring is continued for 2 hours at room temperature
  6. filtrationThe mixture is filtered
  7. customthe solid obtained
  8. washis washed with water and cold ether

Sources & evidence

ORD record
ord-114cfcc6dabc4123acff41fb90438d76
Source dataset
uspto-grants-1995_01
Patent number
US05378728

Reaction notes

Loading…