Hydrochloric Acid → HCID 86739883, compound

HRID 280599Notes

Reaction equation

HRID 280599 reaction equation
[ClH:1].[CH2:2]([O:4][C:5]([C:7]1[CH:16]=[CH:15][C:10]2[S:11][CH:12]=[C:13]([CH3:14])[C:9]=2[CH:8]=1)=[S:6])[CH3:3].[CH2:17]=O>C(Cl)(Cl)Cl.[Cl-].[Zn+2].[Cl-]>[CH2:2]([O:4][C:5]([C:7]1[CH:16]=[CH:15][C:10]2[S:11][C:12]([CH2:17][Cl:1])=[C:13]([CH3:14])[C:9]=2[CH:8]=1)=[S:6])[CH3:3]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 86739881HCID 86739881, compound

Product 1

HCID 86739883HCID 86739883, compound

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 6212ChloroformSolvent

Procedure

Hydrogen chloride was passed for 2 hours through a stirred mixture of 3-methylthiobenzo[b]thiophene-5-carboxylic acid ethyl ester (1.0 g), paraformaldehyde (0.24 g) and anhydrous zinc chloride (0.2 g) in chloroform (30 ml) at 0° C. The resulting mixture was stirred at room temperature for 18 hours and then washed with water. The organic layer was separated, dried (Na2SO4) and evaporated to give an oil which was chromatographed on silica gel. Elution with toluene gave a solid which was crystallised from petrol (b.p. 60°-80°) to give 2-chloromethyl-3-methylthiobenzo[b]thiophene-5-carboxylic acid ethyl ester (0.42 g), m.p. 95°-96°.

Workup

  1. washwashed with water
  2. customThe organic layer was separated
  3. dry with materialdried (Na2SO4)
  4. customevaporated
  5. customto give an oil which
  6. customwas chromatographed on silica gel
  7. washElution with toluene
  8. customgave a solid which
  9. customwas crystallised from petrol (b.p. 60°-80°)

Sources & evidence

ORD record
ord-863c6ac9d9bf4abb8656652be561b69e
Source dataset
uspto-grants-1986_05
Patent number
US04590200

Reaction notes

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