Succinic anhydride → HCID 15551893, compound

HRID 1435904Notes

Reaction equation

HRID 1435904 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([S:8]([N:11]2[C:20](=[O:21])[C:19]3[C:14](=[CH:15][C:16]([Cl:22])=[CH:17][CH:18]=3)[NH:13][C:12]2=[O:23])(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.C1(=O)[O:29][C:27](=[O:28])[CH2:26][CH2:25]1.C1C[O:34][CH2:33]C1>>[Cl:22][C:16]1[CH:15]=[C:14]2[C:19]([C:20](=[O:21])[N:11]([S:8]([C:4]3[CH:3]=[C:2]([NH:1][C:33]([CH:26]([CH3:25])[C:27]([OH:29])=[O:28])=[O:34])[CH:7]=[CH:6][CH:5]=3)(=[O:10])=[O:9])[C:12](=[O:23])[NH:13]2)=[CH:18][CH:17]=1

Participants

4

Reactant 3

HCID 7922Succinic anhydrideHCID 8028TetrahydrofuranHCID 9906468HCID 9906468, compound

Product 1

HCID 15551893HCID 15551893, compoundYield 96%

Procedure

100 mg (0.28 mmol) of Compound 12 was dissolved in 5 ml of THF, 100 mg (1.0 mmol) of succinic anhydride was added, and the resultant mixture was heated and refluxed for 3 hours. The reaction solution was concentrated in vacuo and the crude product thus obtained was crystallized with ethyl acetate-diethyl ether to obtain 120 mg (yield 96%) of the above-identified compound. Properties: colorless crystal, Melting point: 187-188° C., PMR (δ ppm, DMSO-d6): 2.54 (2H, d), 2.59 (2H, d), 7.12 (1H, s), 7.24 (1H, d), 7.59 (1H, t), 7.80 (1H, d), 7.86 (1H, d), 7.96 (1H, d), 8.41 (1H, s), 10.40 (1H, s), 11.63 μL (1H, br), 12.10 (1H, br).

Workup

  1. temperaturerefluxed for 3 hours
  2. concentrationThe reaction solution was concentrated in vacuo
  3. customthe crude product thus obtained
  4. customwas crystallized with ethyl acetate-diethyl ether

Sources & evidence

ORD record
ord-217df43b1adf4464a7a7e72d91214961
Source dataset
uspto-grants-2009_11
Patent number
US07618977B2

Reaction notes

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