Sodium hydride → HCID 58912942, compound

HRID 1971044Notes

Reaction equation

HRID 1971044 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:22](=[O:23])[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15]2=[O:24])=[CH:6][CH:5]=1.[CH3:25][N:26]([CH3:30])[C:27](Cl)=[S:28]>CN(C=O)C>[O:24]=[C:15]1[C:16]2[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:22](=[O:23])[N:14]1[CH2:13][CH2:12][CH2:11][CH2:10][C:7]1[CH:8]=[CH:9][C:4]([O:3][C:27](=[S:28])[N:26]([CH3:30])[CH3:25])=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 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 (60% in mineral oil, 0.44 g, 0.11 mmol) in anhydrous DMF (10 mL) was cooled to 0° C. and added to a solution of 2-[4-(4-hydroxyphenyl)-butyl]isoindole-1,3-dione 8 (2.95 g, 10 mmol) in DMF (15 mL). The mixture was stirred at 0° C. for 30 min and then at room temperature for an additional one hour. A solution of dimethylthiocarbamic acid chloride (1.35 g, 11 mmol) in DMF (10 mL) was then added. The reaction mixture was stirred at room temperature first for 16 h and then at 50° C. for 1 h, cooled back to room temperature and quenched with methanol (10 mL). The mixture was concentrated under vacuum and the residue was purified by flash silica gel column chromatography eluting with CH2Cl2/hexanes/EtOAc (10:1:0.2, v/v) to give the desired product 9 as a yellowish solid (2.27 g, 59% yield). 1H NMR (300 MHz, CDCl3) δ 1.72 (m, 4H), 2.67 (m, 2H), 3.33 (s, 3H), 3.45 (s, 3H), 3.71 (m, 2H), 6.95 (d, 2H), 7.18 (d, 2H), 7.70 (m, 2H), 7.84 (m, 2H). m/z (ESI): 383 [C21H22N2O3S+H]+.

Workup

  1. waitat room temperature for an additional one hour
  2. stirringThe reaction mixture was stirred at room temperature first for 16 h
  3. waitat 50° C. for 1 h
  4. temperaturecooled back to room temperature
  5. customquenched with methanol (10 mL)
  6. concentrationThe mixture was concentrated under vacuum
  7. customthe residue was purified by flash silica gel column chromatography
  8. washeluting with CH2Cl2/hexanes/EtOAc (10:1:0.2

Sources & evidence

ORD record
ord-01f0b10fc781410c8fc3b704d0128453
Source dataset
uspto-grants-2013_04
Patent number
US08431579B2

Reaction notes

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