Sulfuric Acid → HCID 20331137, compound

HRID 2057678Notes

Reaction equation

HRID 2057678 reaction equation
[C:1]([NH:4][C:5]1[CH:17]=[CH:16][C:8]([C:9]([CH2:11][CH2:12][C:13]([OH:15])=[O:14])=[O:10])=[CH:7][CH:6]=1)(=O)[CH3:2].S(=O)(=O)(O)O.[C:23]([O-])(=O)C.[Na+].[Cl:28][C:29]1[CH:34]=[CH:33][C:32]([C:35]#[C:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45]CCBr)=[CH:31][CH:30]=1.C(=O)([O-])[O-].[K+].[K+]>O.CO>[Cl:28][C:29]1[CH:34]=[CH:33][C:32]([C:35]#[C:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:2][CH2:1][NH:4][C:5]2[CH:17]=[CH:16][C:8]([C:9]([CH2:11][CH2:12][C:13]([O:15][CH3:23])=[O:14])=[O:10])=[CH:7][CH:6]=2)=[CH:31][CH:30]=1

Participants

8

Reactant 5

HCID 1118Sulfuric AcidHCID 11430Potassium CarbonateHCID 2323374-(4-Acetamidophenyl)-4-oxobutanoic acidHCID 517045Sodium AcetateHCID 20330966HCID 20330966, compound

Product 1

HCID 20331137HCID 20331137, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
35 °C

Procedure

A mixture of 35 g. of 3-(4-acetamidobenzoyl)propionic acid, 700 ml. of methanol and 1.4 ml. of concentrated sulfuric acid is refluxed for 76 hours. The solution is cooled to 35° C. and poured onto 7 g. of anhydrous sodium acetate while stirring. The reaction mixture is stirred in an ice-bath. The solid is collected and washed with cold methanol to yield methyl 3-(4-aminobenzoyl)priopionate as a white solid. A mixture of this solid, 9.2 g. of 13-(4-chlorophenyl)tridec-12-ynyl bromide and 4.2 g. of potassium carbonate is stirred for 20 hours at 125° C. under nitrogen. The mixture is then cooled to 25° C. and 30 ml. of water is added. After stirring, the product is filtered and washed with water. Recrystallization from methanol affords methyl 3-{4-[13-(4-chlorophenyl)tridec-12-ynylamino]benzoyl}propionate as a white solid.

Workup

  1. additionA mixture of 35 g
  2. additionpoured onto 7 g
  3. customThe solid is collected
  4. washwashed with cold methanol
  5. customto yield methyl 3-(4-aminobenzoyl)priopionate as a white solid
  6. additionA mixture of this solid, 9.2 g
  7. temperatureThe mixture is then cooled to 25° C.
  8. stirringAfter stirring
  9. filtrationthe product is filtered
  10. washwashed with water
  11. customRecrystallization from methanol

Sources & evidence

ORD record
ord-e6c99ce5844e4d078178f04cc7629bd0
Source dataset
uspto-grants-1980_07
Patent number
US04211783

Reaction notes

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