Triethylamine → (NE)-N-[(2-iodophenyl)methylidene]-4-(trifluoromethyl)benzenesulfonamide

HRID 2061589Notes

Reaction equation

HRID 2061589 reaction equation
[I:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.[F:10][C:11]([F:23])([F:22])[C:12]1[CH:17]=[CH:16][C:15]([S:18]([NH2:21])(=[O:20])=[O:19])=[CH:14][CH:13]=1.C(N(CC)CC)C>C(Cl)Cl.C1COCC1.[Ti](Cl)(Cl)(Cl)Cl>[I:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1/[CH:4]=[N:21]/[S:18]([C:15]1[CH:14]=[CH:13][C:12]([C:11]([F:10])([F:23])[F:22])=[CH:17][CH:16]=1)(=[O:19])=[O:20]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 700184-(Trifluoromethyl)benzenesulfonamideHCID 6434392-Iodobenzaldehyde

Product 1

HCID 59268908(NE)-N-[(2-iodophenyl)methylidene]-4-(trifluoromethyl)benzenesulfonamideYield 116%

Reagents, catalysts & solvents 3

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To the mixture of 2-iodobenzaldehyde (11) (12.3 g, 53 mmol) and 4-trifluoromethylbenzenesulfonamide (12) (12.15 g, 54 mmol) in CH2Cl2 (110 mL) and THF (27 mL) was added triethylamine (22.5 mL) and titanium(IV) chloride (3 mL) at 0° C. After stirring at 0° C. for 2 h, the solid was separated via Celite filtration. The filtrate was concentrated under reduced pressure to dryness, triturated with toluene to give 27 g of a yellow solid as the crude product (3) which was used without further purification.

Workup

  1. customthe solid was separated via Celite filtration
  2. concentrationThe filtrate was concentrated under reduced pressure to dryness
  3. customtriturated with toluene

Sources & evidence

ORD record
ord-3208e37bc4e443c8844a8322d7ba3ca7
Source dataset
uspto-grants-2012_10
Patent number
US08283358B2

Reaction notes

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