Hydrochloric Acid → HCID 13770519, compound

HRID 236354Notes

Reaction equation

HRID 236354 reaction equation
[CH2:1]([N:3]1[C:11]2[C:6](=[CH:7][C:8]([C:12]3([CH3:17])[O:16][CH2:15][CH2:14][O:13]3)=[CH:9][CH:10]=2)[CH:5]([C:18]([O:20]CC)=O)[C:4]1=[O:23])[CH3:2].[F:24][C:25]1[CH:31]=[C:30]([F:32])[CH:29]=[CH:28][C:26]=1[NH2:27].Cl.C(Cl)Cl>C1C=CC=CC=1>[F:24][C:25]1[CH:31]=[C:30]([F:32])[CH:29]=[CH:28][C:26]=1[NH:27][C:18]([CH:5]1[C:6]2[C:11](=[CH:10][CH:9]=[C:8]([C:12]3([CH3:17])[O:16][CH2:15][CH2:14][O:13]3)[CH:7]=2)[N:3]([CH2:1][CH3:2])[C:4]1=[O:23])=[O:20]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 97092,4-DifluoroanilineHCID 13770533HCID 13770533, compound

Product 1

HCID 13770519HCID 13770519, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 1.0 g. (3.1 mmoles) of ethyl 1-ethyl-5-(2-methyl-4,5-dihydro-1,3-dioxol-2-yl)oxindole-3-carboxylate and 809 mg. (6.3 mmoles) of 2,4-difluoroaniline in 40 ml of benzene was heated to reflux through a soxhlet filled with 4A sieves for 45 minutes. The reaction mixture was cooled and poured into a mixture of 400 ml. 2N hydrochloric acid and 100 ml. of methylene chloride. The organic layer was separated, dried over magnesium sulfate and concentrated to give 1.24 g. of a solid residue. Recrystallization from diisopropyl ether--methylene chloride gave 1.0 g. of product (80% yield), m.p. 166°-170° C.

Workup

  1. additionA mixture of 1.0 g
  2. temperatureto reflux through a soxhlet
  3. temperatureThe reaction mixture was cooled
  4. additionpoured into a mixture of 400 ml
  5. customThe organic layer was separated
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated
  8. customto give 1.24 g
  9. customRecrystallization from diisopropyl ether
  10. custommethylene chloride gave 1.0 g

Sources & evidence

ORD record
ord-dc70d2af492e4023874fb29a852c0f3f
Source dataset
uspto-grants-1987_02
Patent number
US04644005

Reaction notes

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