Chloroform → HCID 20481321, compound

HRID 1648934Notes

Reaction equation

HRID 1648934 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[S:15][C:9]2[CH2:10][CH2:11][NH:12][CH2:13][CH2:14][C:8]=2[CH:7]=1)=[O:5])[CH3:2].[CH2:16](N(CC)CC)[CH3:17].C(I)C.C(Cl)(Cl)[Cl:27]>>[ClH:27].[CH2:16]([N:12]1[CH2:13][CH2:14][C:8]2[CH:7]=[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[S:15][C:9]=2[CH2:10][CH2:11]1)[CH3:17]

Participants

5

Reactant 4

HCID 6212Chloroform2×HCID 6340Iodoethane2×HCID 8471Triethylamine2×HCID 13072039ethyl 5,6,7,8-tetrahydro-4H-thieno[2,3-d]azepine-2-carboxylate

Product 1

HCID 20481321HCID 20481321, compound

Procedure

6.9 gm (0.0306 mol) of ethyl-5,6,7,8-tetrahydro-4H-thieno[2.3-d]azepine-2-carboxylate were dissolved in 60 ml of chloroform and 4.6 gm=6.4 ml (0.046 mol) of triethylamine, and the solution was heated to boiling. 5.5 gm=2.85 ml (0.035 mol) of ethyl iodide, dissolved in 10 ml of chloroform, were slowly added dropwise while stirring, and the mixture was heated for 3 hours more. After this time, another 1.3 ml of triethylamine and 0.57 ml of ethyl iodide were added. After another 2 hours of boiling, the same compounds were added again in the same quantities. After a total of 7 hours of heating the reaction was finished. The reaction mixture was allowed to cool, and was then extracted three times with water and dried over sodium sulfate. After the chloroform phase had been concentrated by evaporation in a rotary evaporator, 8 gm of a brown oil remained. By dissolving the oil in acetone and mixing the solution with ethereal hydrochloric acid the hydrochloride was precipitated which was then suction-filtered off and recrystallized from isopropyl alcohol.

Workup

  1. additionwere slowly added dropwise
  2. temperaturethe mixture was heated for 3 hours more
  3. additionthe same compounds were added again in the same quantities
  4. temperatureAfter a total of 7 hours of heating the reaction
  5. temperatureto cool
  6. extractionwas then extracted three times with water
  7. dry with materialdried over sodium sulfate
  8. concentrationAfter the chloroform phase had been concentrated by evaporation in a rotary evaporator, 8 gm of a brown oil
  9. dissolutionBy dissolving the oil in acetone
  10. additionmixing the solution with ethereal hydrochloric acid the hydrochloride
  11. customwas precipitated which
  12. filtrationwas then suction-filtered off
  13. customrecrystallized from isopropyl alcohol

Sources & evidence

ORD record
ord-6a86cfd40ae64fd5a0320c4a7bcfab88
Source dataset
uspto-grants-1983_11
Patent number
US04414225

Reaction notes

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