Hydrochloric Acid → 4-(Biphenyl-2-yloxy)-3-cyanobenzenesulfonyl chloride

HRID 1692249

Reaction equation

HRID 1692249 reaction equation
C(N[S:9]([C:12]1[CH:13]=[CH:14][C:15]([O:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[C:16]([CH:19]=1)[C:17]#[N:18])(=[O:11])=[O:10])C1C=CC=CC=1.[ClH:33].Cl[O-].[Na+]>ClCCl>[C:22]1([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=1[O:20][C:15]1[CH:14]=[CH:13][C:12]([S:9]([Cl:33])(=[O:11])=[O:10])=[CH:19][C:16]=1[C:17]#[N:18]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 23665760Sodium HypochloriteHCID 669054565-Benzylsulfamyl-2-(biphenyl-2-yloxy)-benzonitrile

Product 1

HCID 594365064-(Biphenyl-2-yloxy)-3-cyanobenzenesulfonyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 5-benzylsulfamyl-2-(biphenyl-2-yloxy)-benzonitrile (Preparation 56, 6.06 g, 15.4 mmol), dichloromethane and aq HCl was stirred vigorously with cooling (ice bath). Sodium hypochlorite was added dropwise over 30 minutes and stirring continued with cooling for 1 hour. The layers were separated, the aqueous extracted with dichloromethane (2×100ml), and the organic collected, dried (MgSO4) and concentrated in vacuo. The residue was purified using silica gel column chromatography (ethyl acetate:Heptane 10/90 to 20/80) to furnish 4.58 g of the title compound. 1HNMR (CDCl3): δ 6.7 (m, 1H), 7.2-7.6 (m, 9H), 7.85 (m, 1H), 8.15 (m, 1H).

Workup

  1. temperaturewith cooling (ice bath)
  2. stirringstirring
  3. temperaturewith cooling for 1 hour
  4. customThe layers were separated
  5. extractionthe aqueous extracted with dichloromethane (2×100ml)
  6. dry with materialthe organic collected, dried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified

Sources & evidence

ORD record
ord-5c129350de4b462fbbb0f4d8097ae05a
Source dataset
uspto-grants-2012_04
Patent number
US08153814B2

Linked notes

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