Hydrochloric Acid → HCID 59088004, compound

HRID 656282Notes

Reaction equation

HRID 656282 reaction equation
[N:1]1([CH2:7][CH2:8][N:9]2C(=O)C3C(=CC=CC=3)C2=O)[CH2:6][CH2:5][S:4][CH2:3][CH2:2]1.O.NN.Cl.[C:24]([C:28]1[CH:37]=[CH:36][C:31]([CH2:32][N:33]=[C:34]=[S:35])=[CH:30][CH:29]=1)([CH3:27])([CH3:26])[CH3:25]>CO.O1CCCC1.CN(C)C=O.ClCCl.C(N(CC)CC)C>[C:24]([C:28]1[CH:37]=[CH:36][C:31]([CH2:32][NH:33][C:34]([NH:9][CH2:8][CH2:7][N:1]2[CH2:6][CH2:5][S:4][CH2:3][CH2:2]2)=[S:35])=[CH:30][CH:29]=1)([CH3:27])([CH3:25])[CH3:26]

Participants

10

Reactant 4

HCID 313Hydrochloric AcidHCID 24654Hydrazine hydrate (1:1)HCID 144473502-[2-(Thiomorpholin-4-yl)ethyl]-1H-isoindole-1,3(2H)-dioneHCID 148010411-Tert-butyl-4-(isothiocyanatomethyl)benzene

Product 1

HCID 59088004HCID 59088004, compound

Reagents, catalysts & solvents 5

HCID 887MethanolSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

2-(2-thiomorpholin-4-ylethyl)isoindol-1,3-dione 15-1 (2.76 g) was dissolved in a mixture of methanol (20 ml) and tetrahydrofuran (20 ml) and to the solution was added dropwise hydrazine hydrate (550 mg), followed by stirring for 21 hours. To the obtained solution was added 2 N aqueous hydrochloric acid solution (6 ml), and the mixture was stirred for 3 hours and then concentrated under reduced pressure. To the concentrate was added water (15 ml) and the undissolved material was filtered off. The filtrate was concentrated to obtain reaction mixture (1.62 g) as a solid. The obtained mixture (150 mg) was dissolved in dimethylformamide (5 ml) and to the solution was added 4-t-butylbenzylisothiocyanate (210 mg) and a small amount of triethylamine, followed by stirring at room temperature for 23 hours. The resulting mixture was diluted with dichloromethane, washed with water, and concentrated under reduced pressure. The residue was purified by column-chromatography (hexane/ethyl acetate=1/3) to the compound 15-3 (0.12 g) as a white solid.

Workup

  1. stirringthe mixture was stirred for 3 hours
  2. concentrationconcentrated under reduced pressure
  3. additionTo the concentrate was added water (15 ml)
  4. filtrationthe undissolved material was filtered off
  5. concentrationThe filtrate was concentrated
  6. customto obtain
  7. stirringby stirring at room temperature for 23 hours
  8. washwashed with water
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by column-chromatography (hexane/ethyl acetate=1/3) to the compound 15-3 (0.12 g) as a white solid

Sources & evidence

ORD record
ord-1e55c4e29a5947fabbbbb06a7c0ccc94
Source dataset
uspto-grants-2011_12
Patent number
US08071650B2

Reaction notes

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