Dichloromethane → HCID 20540318, compound

HRID 1065304Notes

Reaction equation

HRID 1065304 reaction equation
Cl.C[N:3](C)[C:4](=N)[CH2:5][S:6][C:7](=[O:9])[CH3:8].[S:12]1[CH:16]=[CH:15][CH:14]=[C:13]1[C:17](Cl)=[O:18].ClCCl.C(N(CC)CC)C.C(=O)=[O:31].CC(C)=O>>[S:12]1[CH:16]=[CH:15][CH:14]=[C:13]1[C:17]([NH:3][C:4](=[O:31])[CH2:5][S:6][C:7](=[O:9])[CH3:8])=[O:18]

Participants

6

Reactant 5

HCID 6344Dichloromethane2×HCID 8471TriethylamineHCID 789282-Thiophenecarbonyl chlorideHCID 12837908HCID 12837908, compoundHCID 18522661Acetone cardice

Product 1

HCID 20540318HCID 20540318, compound

Procedure

A reaction mixture comprising 9.8 g. of N, N-dimethyl-2-(acetylthio) acetamidine hydrochloride and 7.0 ml. of thiophene-2-carbonyl chloride in 200 ml. of dichloromethane, under a nitrogen blanket, was cooled to -30° to -48° C., in dry ice/acetone. There was then added 25 ml. of triethylamine in 50 ml. of dichloromethane, and the reaction mixture was allowed to warm to room temperature, where it was kept for 2 hours. The reaction mixture was concentrated in vacuo and the residue was extracted between 300 ml. of dichloromethane, 100 ml. of 2.5 N hydrochloric acid, and 100 ml. of water. The organic layer was separated and the aqueous layer was extracted once with 100 ml. of chloroform. The combined organic layers were washed with water, dried over sodium sulfate, and concentrated to give 13.5 g. of dark brown oil. The oil was chromatographed on 1 kg. of silica gel, eluting with 50% ether/hexane, to give 0.75 g. of final product.

Workup

  1. additionThere was then added 25 ml
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. extractionthe residue was extracted between 300 ml
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was extracted once with 100 ml
  6. washThe combined organic layers were washed with water
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated
  9. customto give 13.5 g
  10. customThe oil was chromatographed on 1 kg
  11. washof silica gel, eluting with 50% ether/hexane
  12. customto give 0.75 g

Sources & evidence

ORD record
ord-2896836874c44f0da6bcf8943b8048b4
Source dataset
uspto-grants-1982_05
Patent number
US04329363

Reaction notes

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