Hydrochloric Acid → HCID 23046974, compound

HRID 2106969Notes

Reaction equation

HRID 2106969 reaction equation
N([O-])=O.[Na+].N[C:6]1[C:7]2[CH:20]=[CH:19][CH:18]=[CH:17][C:8]=2[S:9][C:10]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[S:21]([O-:24])(O)=[O:22].[Na+].[ClH:26]>S([O-])([O-])(=O)=O.[Cu+2]>[C:11]1([C:10]2[S:9][C:8]3[CH:17]=[CH:18][CH:19]=[CH:20][C:7]=3[C:6]=2[S:21]([Cl:26])(=[O:24])=[O:22])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 12415655HCID 12415655, compoundHCID 23665763Sodium Bisulfite2×HCID 23668193Sodium Nitrite

Product 1

HCID 23046974HCID 23046974, compound

Reagents, catalysts & solvents 1

HCID 24462Copper SulfateCatalyst

Procedure

6.9 g (50 mmol) of a 50% solution of sodium nitrite are added dropwise at 0°-5° C. to a suspension of 11.3 g (50 mmol) of 3-amino-2-phenylbenzo[b]thiophene in 40 g of ice water and 20 ml (150 mmol) of 32% hydrochloric acid. After the mixture has been stirred at the same temperature for 15 minutes, it is filtered over silica. This filtrate, together with 13 g (50 mmol) of a 40% solution of sodium hydrogensulfite, is added dropwise at 10°-15° C. to a solution of 1.2 g (5 mmol) of copper sulfate in 13 g (50 mmol) of a 40% solution of sodium hydrogensulfite and in 50 ml of 32% hydrochloric acid. The reaction mixture is stirred for a further 1.5 hours at 20°-25° C. and then extracted with 3×50 ml of methylene chloride. The combined organic extracts contain the desired 2-phenylbenzo[b]thiophen-3-ylsulfonyl chloride and can be used in the following reaction step without further purification.

Workup

  1. filtrationit is filtered over silica
  2. stirringThe reaction mixture is stirred for a further 1.5 hours at 20°-25° C.
  3. extractionextracted with 3×50 ml of methylene chloride
  4. customcan be used in the following reaction step without further purification

Sources & evidence

ORD record
ord-be3624c3f8f54fbdaa9d9b01aa1b9243
Source dataset
uspto-grants-1990_06
Patent number
US04932997

Reaction notes

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