Benzenesulfonyl chloride → HCID 68296415, compound

HRID 631887Notes

Reaction equation

HRID 631887 reaction equation
[C:1]1([S:7](Cl)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:11][C:12]1[CH:19]=[CH:18][CH:17]=[C:16]([Br:20])[C:13]=1[C:14]#[N:15]>C(Cl)Cl.N1C=CC=CC=1>[Br:20][C:16]1[C:13]([C:14]#[N:15])=[C:12]([NH:11][S:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)(=[O:9])=[O:8])[CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 2

HCID 7369Benzenesulfonyl chloride2×HCID 98130382-Amino-6-bromobenzonitrile2×

Product 1

HCID 68296415HCID 68296415, compoundYield 28%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent2×

Procedure

Benzenesulfonyl chloride (0.53 g) was added to a solution of 2-amino-6-bromobenzonitrile (Intermediate 22, 0.5 g) in DCM (15 mL) and pyridine (1 mL). The mixture was stirred for 2 hours, then a further aliquot of benzenesulfonyl chloride (0.53 g) was added and the mixture was stirred overnight. The reaction mixture was diluted with DCM, washed with 1N hydrochloric acid, and the organic solution was dried with sodium sulfate and filtered. The filtrate was evaporated under vacuum and the residue was purified by flash chromatography on silica, eluting with a mixture of DCM and methanol. The fractions containing the desired product were combined and evaporated to give the title compound as a white powder (0.24 g).

Workup

  1. stirringthe mixture was stirred overnight
  2. washwashed with 1N hydrochloric acid
  3. dry with materialthe organic solution was dried with sodium sulfate
  4. filtrationfiltered
  5. customThe filtrate was evaporated under vacuum
  6. customthe residue was purified by flash chromatography on silica
  7. washeluting with a mixture of DCM and methanol
  8. additionThe fractions containing the desired product
  9. customevaporated

Sources & evidence

ORD record
ord-a2facf03a2c94056a10d653fa15c73d6
Source dataset
uspto-grants-2016_04
Patent number
US09321740B2

Reaction notes

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