Triethylamine → HCID 58531520, compound

HRID 1889687Notes

Reaction equation

HRID 1889687 reaction equation
[C:1]1([CH2:17][NH:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][NH:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=1.C(N(CC)CC)C.[Cl:34][C:35]1[CH:36]=[C:37]([S:42](Cl)(=[O:44])=[O:43])[CH:38]=[C:39]([Cl:41])[CH:40]=1>C(Cl)Cl>[Cl:41][C:39]1[CH:38]=[C:37]([S:42]([N:8]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)[CH2:7][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=2[CH2:17][NH:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)(=[O:43])=[O:44])[CH:36]=[C:35]([Cl:34])[CH:40]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 5223883,5-Dichlorobenzenesulfonyl chlorideHCID 66616500HCID 66616500, compound

Product 1

HCID 58531520HCID 58531520, compoundYield 67.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of N,N′-(1,2-phenylenebis(methylene))bis(1-(4-fluorophenyl)methanamine) (1 g, 2.8 mmol, 1 eq) in DCM (HPLC grade 50 mL) at 0° C. was added triethylamine (0.87 g, 8.6 mmol, 3 eq) followed by 3,5-dichlorobenzenesulfonyl chloride (0.52 g, 2.1 mmol, 0.75 eq). The mixture was stirred at 0° C. for 1 h, before being concentrated to dryness. Water was added to the residue and the aqueous mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous Na2SO4 before being evaporated under reduced pressure. The resulting residue was purified by silica gel (230-400) column chromatography eluting with 6% ethyl acetate in hexane to afford the desired product (0.8 g, 53%). 1H NMR (400 MHz, CD3OD) δ 7.76-7.72 (m, 1H), 7.33-7.23 (m, 2H), 7.20-7.17 (m, 2H), 7.13-7.10 (m, 4H), 7.03-6.95 (m, 4H), 6.80-6.77 (m, 2H), 4.80 (s, 2H), 4.30 (s, 2H), 3.70 (s, 2H), 3.60 (s, 2H). MS (ESI): 562.0 (M+H)+.

Workup

  1. concentrationbefore being concentrated to dryness
  2. additionWater was added to the residue
  3. extractionthe aqueous mixture was extracted with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous Na2SO4
  5. custombefore being evaporated under reduced pressure
  6. customThe resulting residue was purified by silica gel (230-400) column chromatography
  7. washeluting with 6% ethyl acetate in hexane

Sources & evidence

ORD record
ord-c31c6966e61f4475a93daafaab2685bc
Source dataset
uspto-grants-2013_08
Patent number
US08501992B2

Reaction notes

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