Phenethylamine → HCID 58932539, compound

HRID 853860Notes

Reaction equation

HRID 853860 reaction equation
[O:1]=[C:2]1[C:10](=[O:11])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([S:12](Cl)(=[O:14])=[O:13])[CH:8]=2)[NH:3]1.C1COCC1.[CH2:21](CN)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[CH:30]([N:33](CC)C(C)C)(C)C>C(Cl)(Cl)Cl>[CH2:21]([N:33]([CH3:30])[S:12]([C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[NH:3][C:2](=[O:1])[C:10]2=[O:11])(=[O:14])=[O:13])[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

6

Reactant 4

HCID 1001PhenethylamineHCID 8028TetrahydrofuranHCID 81531DiisopropylethylamineHCID 159089472,3-Dioxoindoline-5-sulfonyl chloride

Product 1

HCID 58932539HCID 58932539, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a black solution of 2,3-Dioxo-2,3-dihydro-1H-indole-5-sulfonylchloride (4.00 g, 16.3 mmol) in 1:1 THF:CHCl3 was added, drop-wise via syringe pump, a solution of N-benzylmethylamine (2.73 mL, 21.2 mmol, 1.3 eq) and N,N-diisopropylethylamine (5.68 mL, 32.6 mmol, 2 eq) in CHCl3 (32 mL) over a period of 1.25 hr. with cooling in an ice bath. After stirring for 50 min. the reaction was allowed to warm to room temperature and stirred for 30 minutes. The reaction was concentrated. The crude product was purified on Biotage KP silica gel eluting with 98/2 CHCl2/CH3OH to give the analytically pure sample of the title compound as a bright yellow solid (0.18 g, 15% yield). Anal. Calc'd for C16H14N2O4S: C, 58.17; H, 4.27; N, 8.48. Found: C, 57.88; H, 4.36; N, 8.40. MS: (API-ES−) m/z 329 [M−H]. m.p.: 183-185° C.

Workup

  1. temperaturewith cooling in an ice bath
  2. stirringstirred for 30 minutes
  3. concentrationThe reaction was concentrated
  4. customThe crude product was purified on Biotage KP silica gel eluting with 98/2 CHCl2/CH3OH

Sources & evidence

ORD record
ord-59e4b4742c8b421a92a46f61264fd923
Source dataset
uspto-grants-2007_08
Patent number
US07256198B2

Reaction notes

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