Benzyl mercaptan → 3-Benzylsulfanyl-3-(4-chlorophenyl)-2-propylisoindolin-1-one

HRID 2381571Notes

Reaction equation

HRID 2381571 reaction equation
Cl[C:2]1([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH2:12][CH2:13][CH3:14].[CH2:22]([SH:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(OCC)(=O)C>CO>[CH2:22]([S:29][C:2]1([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH2:12][CH2:13][CH3:14])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 7509Benzyl mercaptan2×HCID 8857Ethyl Acetate2×HCID 513512563-Chloro-3-(4-chlorophenyl)-2-propylisoindolin-1-one

Product 1

HCID 598247853-Benzylsulfanyl-3-(4-chlorophenyl)-2-propylisoindolin-1-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Distilled THF was added to 3-chloro-3-(4-chlorophenyl)-2-propylisoindolin-1-one (1.06 g, 3.31 mmol) followed by benzyl mercaptan (0.855 mL, 7.29 mmol) as for general procedure C. On addition of the benzyl mercaptan, a pale pink precipitate formed which turned white over time. The ethyl acetate was mostly removed under vacuum. On leaving overnight in the fridge, clear crystals formed. The crude product was purified by flash column chromatography (20:80, EtOAc:petrol) and recrystallised in the minimum amount of hot ethyl acetate giving large colourless crystals of 3-benzylsulfanyl-3-(4-chlorophenyl)-2-propyl-2,3-dihydroisoindolin-1-one (918 mg, 2.25 mmol, 68%). Rf 0.68 (40:60 EtOAc:petrol). Mp. 131.5-133.4° C. λmax (CH3OH)/nm 223.0, Abs 0.964. IR: 3161, 2968, 1665, 1608, 1467, 1435, 1402 cm−1. 1H NMR (300 Hz, CDCl3); δ 0.72 (t, 3H, J=7.5 Hz, N(CH2)2—CH3), 1.37 (m, 1H, N—CH2—CH2—CH3), 1.57 (m, 1H, N—CH2—CH2—CH3), 2.80 (d, 1H, J=12 Hz, S—CH2), 3.10 (d, 1H, J=12 Hz, S—CH2), 3.17 (m, 1H, N—CH2), 3.36 (m, 1H, N—CH2), 6.92-7.81 (m, 13H, Ar). 13C NMR (75 Hz, CDCl3); 111.8 (N—(CH2)2—CH3), 21.5 (N—CH2—CH2), 33.4 (S—CH2), 42.6 (N—CH2), 78.2 (S—C—N), 123.2, 123.4, 127.3, 128.0, 128.5, 128.9, 128.9, 131.0, 132.8, 134.9, 135.8, 137.1, 148.3 (Ar), 167.9 (C═O). LC/MS-ES+ m/z 410.6, 408.7, 286.1, 287.1. Anal. Calcd. for C24H22ClNOS: C, 70.66; H, 5.44; N, 3.43%. Found C, 70.60; H, 5.51; N, 3.51%.

Workup

  1. distillationDistilled THF
  2. customa pale pink precipitate formed which
  3. customThe ethyl acetate was mostly removed under vacuum
  4. customOn leaving overnight in the fridge, clear crystals
  5. customformed
  6. customThe crude product was purified by flash column chromatography (20:80, EtOAc:petrol)

Sources & evidence

ORD record
ord-8373fc4298f2490abbef401c88df0acb
Source dataset
uspto-grants-2012_09
Patent number
US08258175B2

Reaction notes

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