Phthalimide → N-[(2-Cyanoethyl)thio]phthalimide

HRID 726422Notes

Reaction equation

HRID 726422 reaction equation
ClCl.[C:3]([CH2:5][CH2:6][SH:7])#[N:4].[C:8]1(=[O:18])[NH:12][C:11](=[O:13])[C:10]2=[CH:14][CH:15]=[CH:16][CH:17]=[C:9]12.C(N(CC)CC)C.C(=O)([O-])O.[Na+]>ClCCl.CN(C=O)C>[C:3]([CH2:5][CH2:6][S:7][N:12]1[C:11](=[O:13])[C:10]2=[CH:14][CH:15]=[CH:16][CH:17]=[C:9]2[C:8]1=[O:18])#[N:4]

Participants

8

Reactant 5

HCID 6809PhthalimideHCID 8471TriethylamineHCID 24526ChlorineHCID 70477Propanenitrile, 3-mercapto-HCID 516892Sodium Bicarbonate

Product 1

HCID 4067398N-[(2-Cyanoethyl)thio]phthalimideYield 58%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

A Solution of chlorine in dichloromethane (1.4 mol dm-3, 10.0 cm3, 14.0 mmol) was added dropwise to a stirred solution of 2-cyanoethyl mercaptan, (see, for example, Bauer and Welsh, loc cit), (1.22 g, 14.0 mmol) in dichloromethane (21 cm3) at 0° C. (ice-water bath). After the products had been allowed to warm to room temperature, they were added dropwise to a stirred slurry of phthalimide (1.47 g, 10.0 mmol) and triethylamine (1.94 cm3, 14.0 mmol) in dry DMF (12 cm3) at 0° C. (ice-water bath). The stirred reactants were allowed to warm to room temperature. After 2 h, the products were poured into saturated aqueous sodium hydrogen carbonate (25 cm3) and the resulting mixture was extracted with dichloromethane (2×50 cm3). The combined organic layers were dried (MgSO4) and concentrated under reduced pressure. The residue was crystallized from ethanol to give N-(2-cyanoethylmercapto)phthalimide 21 as colourless needles (1.345 g, 58%) (Found: C, 57.0; H, 3.4; N, 11.8. C11H8 N2O2S requires: C, 56.9; H, 3.5; N, 12.1%), m.p. 162°-164° C.; δH [CDCl3 ] 2.79 (2 H, t, J7.2), 3.12 (2 H, t, J7.2), 7.83 (2 H, m), 7.95 (2 H, m); δC [CDCl3 ] 18.7, 34.5, 117.5, 124.1, 131.7, 134.9, 168.1.

Workup

  1. temperatureto warm to room temperature
  2. extractionthe resulting mixture was extracted with dichloromethane (2×50 cm3)
  3. dry with materialThe combined organic layers were dried (MgSO4)
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was crystallized from ethanol

Sources & evidence

ORD record
ord-05ef8d557b404a5d8dc787c928a66f7d
Source dataset
uspto-grants-1998_01
Patent number
US05708161

Reaction notes

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