Water → HCID 25111366, compound

HRID 1968408Notes

Reaction equation

HRID 1968408 reaction equation
CN(C)C(=O)[S:4][C:5]1[CH:10]=[CH:9][C:8](/[CH:11]=[CH:12]/[C:13]2[CH:18]=[C:17]([O:19][CH3:20])[CH:16]=[C:15]([O:21][CH3:22])[CH:14]=2)=[CH:7][CH:6]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].O>C(OCC)C>[CH3:20][O:19][C:17]1[CH:18]=[C:13]([CH:14]=[C:15]([O:21][CH3:22])[CH:16]=1)/[CH:12]=[CH:11]/[C:8]1[CH:7]=[CH:6][C:5]([SH:4])=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 86667791HCID 86667791, compound

Product 1

HCID 25111366HCID 25111366, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of (E)-S-4-(3,5-dimethoxystyryl)phenyl dimethylcarbamothioate (50 mg, 0.14 mM) in ethyl ether (10 mL) was added LiAlH4 (6 mg, 0.14 mM) at 0° C. The reaction mixture was stirred at 65° C. for 3 h. The mixture was poured into water (10 mL) and a solution of 1M HCL (10 mL). The crude mixture was purified by column chromatography eluting with hexanes:ethyl acetate (4:1) and gave ARS27.

Workup

  1. customThe crude mixture was purified by column chromatography
  2. washeluting with hexanes:ethyl acetate (4:1)
  3. customgave ARS27

Sources & evidence

ORD record
ord-3de2028e05514b3fb286b4942ead9b25
Source dataset
uspto-grants-2013_04
Patent number
US08426369B2

Reaction notes

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