Acetic Acid → HCID 20210844, compound

HRID 1906756Notes

Reaction equation

HRID 1906756 reaction equation
Br[CH2:2][C:3]1[C:8]2[S:9][CH:10]=[C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:7]=2[CH:6]=[CH:5][CH:4]=1.C1N2CN3CN(C2)CN1C3.Cl.C(O)(=[O:31])C>O>[C:12]1([C:11]2[C:7]3[CH:6]=[CH:5][CH:4]=[C:3]([CH:2]=[O:31])[C:8]=3[S:9][CH:10]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 4101HexamethylenetetramineHCID 20210831HCID 20210831, compound

Product 1

HCID 20210844HCID 20210844, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

7-Bromomethyl-3-phenylbenzo[b]thiophene (13.5 g; 44.6 mmole) was added to a solution of hexamine (14.0 g; 0.1 mole) in a mixture of acetic acid (50 ml) and water (25 ml) and the mixture refluxed with stirring for 3.5 hours. Concentrated hydrochloric acid (25 ml) was added and the mixture refluxed for a further 20 minutes. The solution was cooled, poured into water and extracted with diethyl ether. The combined ether extracts were dried over magnesium sulphate and evaporated. The crude product was purified by column chromatography on silica eluting with a mixture of methylene chloride and hexane. The relevant fractions were combined and evaporated to yield 3-phenylbenzo[b]thiophene-7-carboxaldehyde as an oil. (4.9 g).

Workup

  1. temperaturethe mixture refluxed
  2. temperaturethe mixture refluxed for a further 20 minutes
  3. temperatureThe solution was cooled
  4. extractionextracted with diethyl ether
  5. dry with materialThe combined ether extracts were dried over magnesium sulphate
  6. customevaporated
  7. customThe crude product was purified by column chromatography on silica eluting with a mixture of methylene chloride and hexane
  8. customevaporated

Sources & evidence

ORD record
ord-c86e09ccde524e9d8f812d6017a9e709
Source dataset
uspto-grants-1987_03
Patent number
US04654352

Reaction notes

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