Formic Acid → HCID 15582898, compound

HRID 485202Notes

Reaction equation

HRID 485202 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([O:9][CH:10]([C:12]([O:14]CC)=[O:13])[CH3:11])=[CH:4][C:3]=1[N:17]1[C:21](=[O:22])[C:20]2[CH2:23][CH2:24][CH2:25][CH2:26][C:19]=2[C:18]1=[O:27].CS(O)(=O)=O.C(O)=O>O>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([O:9][CH:10]([C:12]([OH:14])=[O:13])[CH3:11])=[CH:4][C:3]=1[N:17]1[C:21](=[O:22])[C:20]2[CH2:23][CH2:24][CH2:25][CH2:26][C:19]=2[C:18]1=[O:27]

Participants

5

Reactant 3

HCID 284Formic AcidHCID 6395Methanesulfonic AcidHCID 15582899HCID 15582899, compound

Product 1

HCID 15582898HCID 15582898, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 14.4 g. of N-[2,4-dichloro-5-(1-ethoxycarbonylethyloxy)phenyl]-3,4,5,6-tetrahydrophthalimide, 3.40 g. of methanesulfonic acid and 35 ml. of 86% formic acid was refluxed with stirring for 15 hours and the reaction mixture was cooled to room temperature and water was added and the product was extracted with ethyl acetate. The extract was concentrated under a reduced pressure and the oily product was admixed with n-hexane and was triturated to obtain the crystals. The product was recrystallized from benzene-cyclohexane to obtain 8.7 g. of Compound No. 11 shown in Table 1.

Workup

  1. additionA mixture of 14.4 g
  2. extractionthe product was extracted with ethyl acetate
  3. concentrationThe extract was concentrated under a reduced pressure
  4. customwas triturated
  5. customto obtain the crystals
  6. customThe product was recrystallized from benzene-cyclohexane
  7. customto obtain 8.7 g

Sources & evidence

ORD record
ord-294457b4240342a6baf0e581958d0f96
Source dataset
uspto-grants-1985_08
Patent number
US04536209

Reaction notes

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