Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → HCID 15675561, compound

HRID 1614207Notes

Reaction equation

HRID 1614207 reaction equation
[NH2:1][C:2]1[CH:18]=[CH:17][CH:16]=[CH:15][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([O:13][CH3:14])[CH:8]=1)=[O:5].CC1(C)OC(=O)[CH:23]([CH:27]([C:34]2[C:42]3[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=3)[NH:36][CH:35]=2)[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:22](=O)O1.CC1C=CC(S([O-])(=O)=O)=CC=1.C1C=C[NH+]=CC=1>N1C=CC=CC=1>[C:28]1([CH:27]([C:34]2[C:42]3[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=3)[NH:36][CH:35]=2)[CH2:23][C:22]2[N:6]([C:7]3[CH:12]=[CH:11][CH:10]=[C:9]([O:13][CH3:14])[CH:8]=3)[C:4](=[O:5])[C:3]3[C:2](=[CH:18][CH:17]=[CH:16][CH:15]=3)[N:1]=2)[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

5

Reactant 3

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 24422032-amino-N-(3-methoxyphenyl)benzamideHCID 111318571,3-Dioxane-4,6-dione, 5-(1H-indol-3-ylphenylmethyl)-2,2-dimethyl-

Product 1

HCID 15675561HCID 15675561, compoundYield 25.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2-Amino-N-(3-methoxyphenyl)benzamide (2.77 g, 11.5 mmol), 3-[α-(2,2-dimethyl-4,6-dioxo-1,3-dioxane-5-yl)benzyl]indole (4.00 g, 11.5 mmol), and PPTS (1.44 g, 5.7 mmol) in 20 ml of pyridine was refluxed for seven days. The reaction mixture was concentrated in vacuo to an oil and partitioned between ethyl acetate and water. The ethyl acetate layer was separated, washed (1N hydrochloric acid, saturated sodium bicarbonate, and brine), dried over anhydrous sodium sulfate, and concentrated in vacuo to dryness. The reaction was incomplete. The product was therefore mixed with PPTS (3 g) and 10 ml of 2,4,6-collidine and refluxed for five hours. The product was worked up as above to provide an oil which, upon standing for about one month, began to crystallize. Trituration with ethyl acetate and filtration provided 1.4 g of the title product: mp 160°-164° C.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo to an oil
  2. custompartitioned between ethyl acetate and water
  3. customThe ethyl acetate layer was separated
  4. washwashed (1N hydrochloric acid, saturated sodium bicarbonate, and brine)
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo to dryness
  7. additionThe product was therefore mixed with PPTS (3 g) and 10 ml of 2,4,6-collidine
  8. temperaturerefluxed for five hours
  9. customto provide an oil which
  10. waitupon standing for about one month
  11. customto crystallize
  12. filtrationTrituration with ethyl acetate and filtration

Sources & evidence

ORD record
ord-dfb4a154ddb04a06a0f4e88b2f58cb13
Source dataset
uspto-grants-1993_03
Patent number
US05196427

Reaction notes

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