Sulfuric Acid → HCID 10812046, compound

HRID 1288817Notes

Reaction equation

HRID 1288817 reaction equation
[NH2:1][C:2]1[S:3][C:4]([CH3:20])=[C:5]([CH3:19])[C:6]=1[C:7](=O)[C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[C:10]([O:16][CH3:17])[CH:9]=1.[Cl:21][CH2:22][C:23](=O)[CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26].S(=O)(=O)(O)O>C(O)(=O)C>[Cl:21][CH2:22][C:23]1[N:1]=[C:2]2[S:3][C:4]([CH3:20])=[C:5]([CH3:19])[C:6]2=[C:7]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[C:10]([O:16][CH3:17])[CH:9]=2)[C:24]=1[C:25]([O:27][CH2:28][CH3:29])=[O:26]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 69484Ethyl 4-chloroacetoacetateHCID 858786HCID 858786, compound

Product 1

HCID 10812046HCID 10812046, compoundYield 67.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 2-amino-3-(3,4-dimethoxybenzoyl)-4,5-dimethylthiophene (3.6 g), ethyl 4-chloroacetoacetate (2.1 g), concentrated sulfuric acid (0.5 ml) and acetic acid (50 ml) was stirred for two hours at temperature ranging from 90° to 100° C. The reaction mixture was concentrated under reduced pressure. The concentrate was poured into water, which was neutralized with potassium carbonate, followed by extraction with chloroform. The chloroform layer was washed with water and dried (MgSO4), then the solvent was distilled off under reduced pressure. The residue was subjected to column chromatography on silica gel. From the fractions eluted with chloroform-hexane (4:1, v/v), ethyl 6-chloromethyl-4-(3,4-dimethoxyphenyl)-2,3-dimethylthieno[2,3-b]pyridine-5-carboxylate (3.5 g, 67%) was obtained. Recrystallization from ethyl acetate-hexane gave colorless prisms, m.p.162°-163° C.

Workup

  1. customranging from 90° to 100° C
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additionThe concentrate was poured into water, which
  4. extractionfollowed by extraction with chloroform
  5. washThe chloroform layer was washed with water
  6. dry with materialdried (MgSO4)
  7. distillationthe solvent was distilled off under reduced pressure
  8. washFrom the fractions eluted with chloroform-hexane (4:1

Sources & evidence

ORD record
ord-a7302598297b425db538654560130c98
Source dataset
uspto-grants-1998_05
Patent number
US05747486

Reaction notes

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