Acetic Acid → HCID 15410533, compound

HRID 1066398Notes

Reaction equation

HRID 1066398 reaction equation
[C:1]([C:3]([C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([Cl:19])[CH:13]=1)([CH2:8]CC#N)[CH2:4][C:5](O)=[O:6])#[N:2].S(=O)(=O)(O)[OH:21].[OH2:25].[C:26]([OH:29])(=O)[CH3:27]>>[C:5]([CH2:4][C:3]1([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([Cl:19])[CH:13]=2)[CH2:8][CH2:27][C:26](=[O:29])[NH:2][C:1]1=[O:21])([OH:6])=[O:25]

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 1118Sulfuric AcidHCID 21200304HCID 21200304, compound

Product 1

HCID 15410533HCID 15410533, compound

Conditions

Temperature
80 °C

Procedure

20 g of the derivative prepared according to (a) in 80 ml of acetic acid are introduced into a round-bottomed flask. 6.75 ml of 80% sulphuric acid are then added dropwise and the reaction mixture is heated to 80° C. and then under reflux for 1 hour and 30 minutes. The reaction mixture is then left to return to room temperature and 240 ml of iced water are added to it. After stirring at 10° C. for 30 minutes, the precipitate is separated off by filtration. The precipitate is taken up into 130 ml of acetic acid which is then distilled off in order to obtain a residue which crystallises providing 17 g of the expected product (Formula (I), X=CH2, Ar=3,4-dichlorophenyl); M. Pt.=203° C.

Workup

  1. custom20 g of the derivative prepared
  2. additionare introduced into a round-bottomed flask
  3. temperatureunder reflux for 1 hour and 30 minutes
  4. waitThe reaction mixture is then left
  5. customto return to room temperature
  6. customthe precipitate is separated off by filtration
  7. distillationis then distilled off in order
  8. customto obtain a residue which
  9. customcrystallises

Sources & evidence

ORD record
ord-72fa0c4ae45f424b961d801787bc497c
Source dataset
uspto-grants-2001_06
Patent number
US06242607B1

Reaction notes

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