Hydrochloric Acid → 7-Oxo-4,5,6,7-tetrahydrobenzo[b]thiophene-3-sulfonyl chloride

HRID 1351246Notes

Reaction equation

HRID 1351246 reaction equation
[ClH:1].N[C:3]1[C:4]2[CH2:11][CH2:10][CH2:9][C:8](=[O:12])[C:5]=2[S:6][CH:7]=1.Cl.CC(OCC1C2C(=CC=CC=2)C(COC(C)=O)=C2C=1C=CC=C2)=O.[S:38](=[O:42])(=O)(O)[OH:39].N([O-])=O.[Na+].S(=O)(O)O>O.O.[Cu](Cl)Cl.C(O)(=O)C>[O:12]=[C:8]1[C:5]2[S:6][CH:7]=[C:3]([S:38]([Cl:1])(=[O:42])=[O:39])[C:4]=2[CH2:11][CH2:10][CH2:9]1

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 1100Sulfurous AcidHCID 1118Sulfuric AcidHCID 613145Acetic acid 10-acetoxymethyl-anthracen-9-ylmethyl esterHCID 21098612HCID 21098612, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 210986857-Oxo-4,5,6,7-tetrahydrobenzo[b]thiophene-3-sulfonyl chloride

Reagents, catalysts & solvents 2

HCID 61482Cupric chloride dihydrateCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
5 °C

Procedure

3-Amino-5,6-dihydro-4H-benzo[b]thiophene-7-one hydrochloride (13.8 g) was suspended in a mixture solution of concentrated hydrochloric acid (43 mL), acid acetic (50 mL) and concentrated sulfuric acid (7 mL). An aqueous solution (8.4 mL) of sodium nitrite (5 g) was added dropwise on an ice bath while stirring vigorously so as to maintain the internal temperature at 5° C. or lower. After stirring for 30 minutes, to this reaction solution was added a solution of acetic acid (56 mL) containing copper (II) chloride dihydrate (1.35 g) saturated with sulfurous acid gas. The solution was warmed to room temperature and stirred at room temperature for 3 hours. The reaction solution was poured into ice water and extracted twice with ethyl acetate. After washing the organic layer twice with water and once with saturated sodium chloride water, and then dried with anhydrous magnesium sulfate. The solvent was evaporated at reduced pressure to provide the title compound (14.8 g) as a tango candy-like substance.

Workup

  1. stirringAfter stirring for 30 minutes, to this reaction solution
  2. temperatureThe solution was warmed to room temperature
  3. stirringstirred at room temperature for 3 hours
  4. extractionextracted twice with ethyl acetate
  5. washAfter washing the organic layer twice with water
  6. dry with materialonce with saturated sodium chloride water, and then dried with anhydrous magnesium sulfate
  7. customThe solvent was evaporated at reduced pressure

Sources & evidence

ORD record
ord-a18f23d684394ba1b90e55c91bdaca75
Source dataset
uspto-grants-2007_05
Patent number
US07217723B2

Reaction notes

Loading…