Sulfur → 5,5'-Sulfanediylbis(2-phenyl-1H-isoindole-1,3(2H)-dione)

HRID 1607716Notes

Reaction equation

HRID 1607716 reaction equation
[S:1]([C:19]1[CH2:20][CH:21]2[C:26](=[O:27])[N:25]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:23](=[O:24])[CH:22]2[CH2:34][CH:35]=1)[C:2]1[CH2:3][CH:4]2[C:9](=[O:10])[N:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:6](=[O:7])[CH:5]2[CH2:17][CH:18]=1.[S]>>[S:1]([C:2]1[CH:3]=[C:4]2[C:9](=[O:10])[N:8]([C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:6](=[O:7])[C:5]2=[CH:17][CH:18]=1)[C:19]1[CH:20]=[C:21]2[C:26](=[O:27])[N:25]([C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)[C:23](=[O:24])[C:22]2=[CH:34][CH:35]=1

Participants

3

Reactant 2

HCID 5362487SulfurHCID 13860170HCID 13860170, compound

Product 1

HCID 138601735,5'-Sulfanediylbis(2-phenyl-1H-isoindole-1,3(2H)-dione)Yield 31.2%

Procedure

A mixture of 200 mg (0.41 mmol) of 4,4'-thiobis(N-phenyl-1,2,3,6-tetrahydrophthalimide) and 53 mg (1.7 mmol) of elemental sulfur was heated to 240°-260° C. (sand bath) for 20 minutes and cooled to room temperature. The resulting brown residue was purified by preparative TLC on silica gel (eluent: 1% methanol in dichloromethane) to give 61 mg (31% yield) of 4,4'-thiobis(N-phenylphthalimide) as a yellow solid. Trituration with dichloromethane afforded a white solid: mp 275°-280° C.; (lit 293°-295° C.--see U.S. Pat. No. 3,989,712); IR (KBr) 3065, 1710,1375 cm-1 ; 1H NMR (slurry in DMSO-d6) 7.52 (m,5H), 7.97 (m, 3H).

Workup

  1. temperaturewas heated to 240°-260° C. (sand bath) for 20 minutes
  2. customThe resulting brown residue was purified by preparative TLC on silica gel (eluent: 1% methanol in dichloromethane)

Sources & evidence

ORD record
ord-a9429bfb236849eb9bcc43bf62f923fd
Source dataset
uspto-grants-1989_09
Patent number
US04866184

Reaction notes

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