Methanol → HCID 58912942, compound

HRID 747901Notes

Reaction equation

HRID 747901 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][CH2:12][CH2:13][N:14]2[C:18](=[O:19])[C:17]3=[CH:20][CH:21]=[CH:22][CH:23]=[C:16]3[C:15]2=[O:24])=[CH:6][CH:5]=1.[CH3:25][N:26]([CH3:30])[C:27](Cl)=[S:28].CO>CN(C=O)C>[CH3:25][N:26]([CH3:30])[C:27]([O:3][C:4]1[CH:5]=[CH:6][C:7]([CH2:10][CH2:11][CH2:12][CH2:13][N:14]2[C:18](=[O:19])[C:17]3=[CH:20][CH:21]=[CH:22][CH:23]=[C:16]3[C:15]2=[O:24])=[CH:8][CH:9]=1)=[S:28]

Participants

6

Reactant 4

HCID 887MethanolHCID 24758Sodium hydrideHCID 27871Dimethylthiocarbamoyl chlorideHCID 220544512-[4-(4-Hydroxyphenyl)butyl]-1H-isoindole-1,3(2H)-dione

Product 1

HCID 58912942HCID 58912942, compoundYield 59.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Conditions

Temperature
0 °C

Procedure

A suspension of sodium hydride in mineral oil (0.44 g of 60%) in anhydrous DMF (10 mL) was cooled to 0° C. N-[4-(4-hydroxyphenyl)butyl]phthalimide (2.95 g, 10 mmol) dissolved in dry DMF (15 ml) was added into the mixture which was then stirred for 30 min at 0° C. and allowed to warm to room temperature over 1 h. To the mixture was added portionwise N,N-dimethylthiocarbamoyl chloride (1.35 g, 11 mmol) dissolved in DMF (10 ml). The newly formed mixture was stirred at room temperature overnight, then at 50° C. for 1 h, and was cooled back to room temperature, at which point methanol (10 mL) was added into the mixture. The solvent was removed under reduced pressure. The residue was purified by flash chromatography over silica gel (dichloromethane/hexane/ethyl acetate, 10:1:0.2, v/v) to give N-{4-[4-(dimethythiocarbamoyloxy)phenyl]butyl}phthalimide 34 (2.27 g, 59%) as a slightly yellow solid. 1H NMR (300 MHz, CDCl3) δ 1.72 (m, 4H), 2.66 (m, 2H), 3.33 (s, 3H), 3.45 (s, 3H), 3.70 (m, 2H), 6.96 (d, 2H), 7.18 (d, 2H), 7.71 (m, 2H), 7.84 (m, 2H). m/z (ESI) 383 [C21H22N2O3S+H]+.

Workup

  1. additionwas added into the mixture which
  2. temperatureto warm to room temperature over 1 h
  3. stirringThe newly formed mixture was stirred at room temperature overnight
  4. waitat 50° C. for 1 h
  5. additionwas added into the mixture
  6. customThe solvent was removed under reduced pressure
  7. customThe residue was purified by flash chromatography over silica gel (dichloromethane/hexane/ethyl acetate, 10:1:0.2, v/v)

Sources & evidence

ORD record
ord-3398084879184d0bac1328d0344f0348
Source dataset
uspto-grants-2008_07
Patent number
US07399766B2

Reaction notes

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