Sulfur Dioxide → HCID 23046970, compound

HRID 2106971Notes

Reaction equation

HRID 2106971 reaction equation
N[C:2]1[C:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[CH:5][S:4][C:3]=1[C:13]([O:15][CH3:16])=[O:14].N([O-])=O.[Na+].[Cl:21]C(Cl)C.[S:25](=[O:27])=[O:26]>Cl.O.[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.[Cu]Cl.[Cu](Cl)Cl>[CH3:16][O:15][C:13]([C:3]1[S:4][CH:5]=[C:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:2]=1[S:25]([Cl:21])(=[O:27])=[O:26])=[O:14]

Participants

10

Reactant 4

HCID 1119Sulfur DioxideHCID 63651,1-DichloroethaneHCID 2759782Methyl 3-amino-4-phenylthiophene-2-carboxylateHCID 23668193Sodium Nitrite2×

Product 1

HCID 23046970HCID 23046970, compound

Reagents, catalysts & solvents 5

HCID 24014Cupric ChlorideCatalystHCID 62652Cuprous chlorideCatalystHCID 66133Benzyl triethylammonium chlorideCatalystHCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

10.9 g (0.04 mol) of 3-amino-2-methoxycarbonyl-4-phenylthiophene are dissolved in 20 ml of concentrated hydrochloric acid and then diazotised at -5° C. with 3.65 g of sodium nitrite in 10 ml of water. 30 minutes after the dropwise addition of sodium nitrite, the solution of the diazonium salt is added in portions to a mixture of 20 ml of dichloroethane, 0.45 g of benzyltriethylammonium chloride, 0.3 g of copper(I) chloride, 0.3 g of copper(II) chloride and 6 g of sulfur dioxide. When the addition at 5°-10° C. of the solution of the diazonium salt is complete, the reaction mixture is stirred for 1 hour at room temperature and then extracted three times with dichloroethane. The combined extracts are treated with activated carbon, filtered and concentrated. The resultant 2-methoxycarbonyl-4-phenylthiophen-3-ylsulfonyl chloride can be used further in the following reaction step without purification.

Workup

  1. extractionextracted three times with dichloroethane
  2. additionThe combined extracts are treated with activated carbon
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe resultant 2-methoxycarbonyl-4-phenylthiophen-3-ylsulfonyl chloride can be used further in the following reaction step without purification

Sources & evidence

ORD record
ord-94479f14225a4e0ea01f45d109e7ad35
Source dataset
uspto-grants-1990_06
Patent number
US04932997

Reaction notes

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