Water → HCID 19743103, compound

HRID 2254672Notes

Reaction equation

HRID 2254672 reaction equation
[Cl:1][C:2]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[C:3](Cl)=[O:4].[OH-:18].[Na+].[CH:20]([N:23]([CH2:27][CH2:28][NH2:29])[CH:24]([CH3:26])[CH3:25])([CH3:22])[CH3:21].O>C(Cl)Cl>[ClH:1].[CH:20]([N:23]([CH:24]([CH3:26])[CH3:25])[CH2:27][CH2:28][NH:29][C:3](=[O:4])[C:2]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[OH:18])([CH3:22])[CH3:21]

Participants

6

Reactant 4

HCID 962WaterHCID 84591,2-Ethanediamine, N1,N1-bis(1-methylethyl)-HCID 14798Sodium HydroxideHCID 179412902-98-9

Product 1

HCID 19743103HCID 19743103, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

10 g (38 mmole) of 2-chloro-2,2-diphenylacetyl chloride were slowly added to a chilled solution of 7.6 ml 5M sodium hydroxide (38 mmole) and 5.3 g (38 mmole) of diisopropylaminoethylamine in 50 ml of methylene chloride. The temperature was kept at 0° C. with good agitation. The mixture was stirred for 1 h. The water solution was discarded and the organic layer was washed with water and dried over anhydrous sodium sulfate. The solution was evaporated to dryness and the remaining oil solidified. The product was dissolved in 2M hydrochloric acid and heated for 10 min on a steambath to hydrolyze the 2-chloro to a hydroxyl group. The solution was chilled to room temperature and was extracted with methylene chloride. The methylene chloride solution was evaporated and the product was crystallised from warm acetone.

Workup

  1. customwas kept at 0° C. with good agitation
  2. washthe organic layer was washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solution was evaporated to dryness
  5. dissolutionThe product was dissolved in 2M hydrochloric acid
  6. temperatureheated for 10 min on a steambath
  7. extractionwas extracted with methylene chloride
  8. customThe methylene chloride solution was evaporated
  9. customthe product was crystallised
  10. temperaturefrom warm acetone

Sources & evidence

ORD record
ord-9919b6fe2ff642c9ac9f3794d9494312
Source dataset
uspto-grants-1993_08
Patent number
US05236956

Reaction notes

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