Hydrochloric Acid → (3,4-Dichloro-1,2-thiazol-5-yl)(3-thienyl)methanone

HRID 875194Notes

Reaction equation

HRID 875194 reaction equation
[Cl:1][C:2]1[C:6]([Cl:7])=[C:5]([C:8](N(OC)C)=[O:9])[S:4][N:3]=1.I[Mg][C:16]1[CH:20]=[CH:19][S:18][CH:17]=1.Cl>O1CCCC1>[Cl:1][C:2]1[C:6]([Cl:7])=[C:5]([C:8]([C:16]2[CH:20]=[CH:19][S:18][CH:17]=2)=[O:9])[S:4][N:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 866507333,4-dichloro-N-methoxy-N-methyl-1,2-thiazole-5-carboxamideHCID 178506590HCID 178506590, compound

Product 1

HCID 66887208(3,4-Dichloro-1,2-thiazol-5-yl)(3-thienyl)methanoneYield 65%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 3,4-dichloro-N-methoxy-N-methyl-1,2-thiazole-5-carboxamide (3.80 g, 15.7 mmol) in tetrahydrofuran (130 mL) at −5° C. was added dropwise a solution of iodo(3-thienyl)magnesium in tetrahydrofuran (0.3 M, 158 mL, 47.4 mmol). After stirring at room temperature for 72 h, the reaction was worked-up by the addition of aq. HCl (1 M) until pH<7. After removal of the tetrahydrofuran in vacuo, the aqueous phase was extracted with ethyl acetate (3×50 mL). The organic layers were combined, dried over MgSO4 and concentrated in vacuo. The residue was purified on silica gel to afford (3,4-dichloro-1,2-thiazol-5-yl)(3-thienyl)methanone [3.00 g, yield 65%; HPLC/MS: m/z=264 (M+H); log P(HCOOH)=3.31].

Workup

  1. customAfter removal of the tetrahydrofuran in vacuo
  2. extractionthe aqueous phase was extracted with ethyl acetate (3×50 mL)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified on silica gel

Sources & evidence

ORD record
ord-35e2e4cbb57a4bd086d290925e3620ae
Source dataset
uspto-grants-2015_03
Patent number
US08981111B2

Reaction notes

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