Benzenesulfonyl chloride → N-(2-Cyano-3-cyclopropylphenyl)-benzenesulfonamide

HRID 631877Notes

Reaction equation

HRID 631877 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]([CH:20]2[CH2:22][CH2:21]2)[C:13]=1[C:14]#[N:15].C(N(CC)CC)C>C(Cl)Cl.N1C=CC=CC=1>[C:14]([C:13]1[C:16]([CH:20]2[CH2:22][CH2:21]2)=[CH:17][CH:18]=[CH:19][C:12]=1[NH:11][S:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)(=[O:9])=[O:8])#[N:15]

Participants

6

Reactant 3

HCID 7369Benzenesulfonyl chloride2×HCID 8471TriethylamineHCID 667472522-Amino-6-cyclopropylbenzonitrile2×

Product 1

HCID 68296410N-(2-Cyano-3-cyclopropylphenyl)-benzenesulfonamideYield 39.4%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

Benzenesulfonyl chloride (0.093 g) was added to a solution of 2-amino-6-cyclopropyl-benzonitrile (Intermediate 10, 0.07 g) in DCM (4 mL) and pyridine (0.1 mL). The mixture was stirred for 5 hours, then a further aliquot of benzenesulfonyl chloride (0.093 g) was added together with triethylamine (0.12 mL) and the mixture was stirred overnight. The reaction mixture was washed with water, and the organic solution was dried with magnesium sulfate, filtered and the filtrate was evaporated under vacuum. The residue was purified by flash chromatography on silica, eluting with a mixture of ethyl acetate and cyclohexane. The fractions containing the desired product were combined and evaporated to give the title compound as a colorless oil (0.052 g).

Workup

  1. stirringthe mixture was stirred overnight
  2. washThe reaction mixture was washed with water
  3. dry with materialthe organic solution was dried with magnesium 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 ethyl acetate and cyclohexane
  8. additionThe fractions containing the desired product
  9. customevaporated

Sources & evidence

ORD record
ord-28c9045e40b843c8a60b74027cf27e2a
Source dataset
uspto-grants-2016_04
Patent number
US09321740B2

Reaction notes

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