Hydrochloric Acid → HCID 13477609, compound

HRID 370852Notes

Reaction equation

HRID 370852 reaction equation
[C:1]([C:4]1[CH:18]=[CH:17][C:7]([O:8][CH2:9][C:10]2[CH:11]=[C:12]([CH:14]=[CH:15][CH:16]=2)[NH2:13])=[CH:6][C:5]=1[OH:19])(=[O:3])[CH3:2].C(N(CC)CC)C.[C:27]([CH2:31][CH2:32][C:33](Cl)=[O:34])([O:29][CH3:30])=[O:28].Cl>O1CCCC1>[C:1]([C:4]1[CH:18]=[CH:17][C:7]([O:8][CH2:9][C:10]2[CH:11]=[C:12]([NH:13][C:33](=[O:34])[CH2:32][CH2:31][C:27]([O:29][CH3:30])=[O:28])[CH:14]=[CH:15][CH:16]=2)=[CH:6][C:5]=1[OH:19])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 73888Butanoic acid, 4-chloro-4-oxo-, methyl esterHCID 13477607HCID 13477607, compound

Product 1

HCID 13477609HCID 13477609, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-[(4-acetyl-3-hydroxyphenoxy)methyl]aniline (3.4 g prepared as in Example 1B) and triethylamine (1.62 g) in tetrahydrofuran (40 ml) is cooled to -78° C. under nitrogen. To this solution is added 3-carbomethoxypropanoyl chloride (2 g, neat), dropwise. The reaction is left to warm to room temperature overnight, then poured onto 10% HCl and extracted with ether. The extracts are washed with saturated brine, and then dried over MgSO4, and concentrated on a rotary evaporator. The residue is dissolved in a minimum amount of acetone, to which several drops of ether are added and then stored at 0° C. Filtration gives 2.6 g (53% yield) of product, m.p. 121°-123° C.

Workup

  1. waitThe reaction is left
  2. extractionextracted with ether
  3. washThe extracts are washed with saturated brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated on a rotary evaporator
  6. dissolutionThe residue is dissolved in a minimum amount of acetone, to which several drops of ether
  7. additionare added
  8. customstored at 0° C
  9. filtrationFiltration

Sources & evidence

ORD record
ord-1ba2652413e84de8b74fa4d13ca8b2e1
Source dataset
uspto-grants-1985_07
Patent number
US04528392

Reaction notes

Loading…