Triethylamine → HCID 86745649, compound

HRID 1029912Notes

Reaction equation

HRID 1029912 reaction equation
[S:1]1[CH:6]=[C:5]([CH2:7][C:8]([OH:10])=O)[CH2:4][S:3][CH2:2]1.Cl.[C:12]1([C:18]2([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH:26]3[CH:22]([CH2:23][NH:24][CH2:25]3)[C:21](=[O:27])[CH2:20][CH2:19]2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(N(CC)CC)C>ClCCl>[C:28]1([C:18]2([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH:26]3[CH:22]([CH2:23][N:24]([C:8](=[O:10])[CH2:7][C:5]4[CH2:4][S:3][CH2:2][S:1][CH:6]=4)[CH2:25]3)[C:21](=[O:27])[CH2:20][CH2:19]2)[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 19899900HCID 19899900, compoundHCID 212645437,7-Diphenylhexahydro-1H-isoindol-4(2H)-one hydrochloride

Product 1

HCID 86745649HCID 86745649, compoundYield 61.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

N,N'-Carbonyldiimidazole (1.13 g) is added to a solution of 2-(1,3-dithiin-5-yl)acetic acid (1.23 g) in dry dichloromethane (30 cc), cooled to +5° C. The mixture is stirred for 20 minutes at +5° C. and a solution of (3aRS,7aRS)-7,7-diphenyl-4-perhydroisoindolone hydrochloride (2.3 g) and triethylamine (0.98 cc) in dichloromethane (40 cc) is then added. The reaction mixture is stirred for 16 hours at 20° C. The reaction mixture is washed with distilled water (3×50 cc), dried over magnesium sulphate and filtered and the filtrate is concentrated to dryness under reduced pressure (2.7 kPa). The residue is crystallized from acetonitrile (80 cc). The crystals are drained, washed with isopropyl ether (10 cc) and dried. (3aRS,7aRS)-7,7-diphenyl-2-[2-(1,3-dithiin-5-yl)acetyl]-4-perhydroisoindolone (1.94 g) melting at 211° C. is obtained.

Workup

  1. temperaturecooled to +5° C
  2. stirringThe reaction mixture is stirred for 16 hours at 20° C
  3. washThe reaction mixture is washed with distilled water (3×50 cc)
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationthe filtrate is concentrated to dryness under reduced pressure (2.7 kPa)
  7. customThe residue is crystallized from acetonitrile (80 cc)
  8. washwashed with isopropyl ether (10 cc)
  9. customdried

Sources & evidence

ORD record
ord-7a12c3014a0d4ed183168b961dbc718d
Source dataset
uspto-grants-1992_04
Patent number
US05102667

Reaction notes

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