Hydrochloric Acid → HCID 25024042, compound

HRID 1645318Notes

Reaction equation

HRID 1645318 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[S:13](=O)[C:12]3[CH:15]=[C:16]([O:19][C:20](=[O:26])[N:21]([CH2:24][CH3:25])[CH2:22][CH3:23])[CH:17]=[CH:18][C:11]=3[C:10]=2[O:27][C:28]2[CH:33]=[CH:32][C:31]([O:34][CH2:35][CH2:36][N:37]3[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]3)=[CH:30][CH:29]=2)=[CH:5][CH:4]=1.CO.Cl.S([O-])([O-])(=O)=S.[Na+].[Na+]>CCCCCCC.COC(C)(C)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[S:13][C:12]3[CH:15]=[C:16]([O:19][C:20](=[O:26])[N:21]([CH2:22][CH3:23])[CH2:24][CH3:25])[CH:17]=[CH:18][C:11]=3[C:10]=2[O:27][C:28]2[CH:29]=[CH:30][C:31]([O:34][CH2:35][CH2:36][N:37]3[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]3)=[CH:32][CH:33]=2)=[CH:7][CH:8]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 24477Sodium ThiosulfateHCID 44249710HCID 44249710, compound

Product 1

HCID 25024042HCID 25024042, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 8900HeptaneSolventHCID 15413tert-Butyl methyl etherSolvent

Conditions

Temperature
30 °C

Procedure

To a 500 mL flask (fitted with a stir bar) add diethyl-carbamic acid 2-(4-methoxy-phenyl)-1-oxo-3-[4-(2-piperidin-1-yl-ethoxy)-phenoxy]-1H-1Lambda*4*-benzo[b]thiophen-6-yl ester (8.46 mmoles; 5.00 g) and methanol (50.00 mL) at ambient temperature. To the resulting yellow slurry, add 36.5% hydrogen chloride (67.71 mmoles; 5.82 mL; 6.76 g) dropwise over 10 minutes to form a yellow solution. Then add solid sodium thiosulfate (25.39 mmoles; 4.06 g). Stir the resulting yellow mixture at 30° C. for 30 minutes and then quench with 100 mL of EtOAc and 200 mL of 0.5 N NaOH. Transfer the mixture to a separation funnel, separate the organic layer, and wash the organic layer with 100 mL of water and 50 mL of brine. Dry over sodium sulfate and concentrate which results in a thick oil. Dissolve the thick oil into 20 mL of t-butyl methyl ether (MTBE) and then add 50 mL of heptane. Stir the white slurry at room temperature overnight. Collect the white solid by filtration and wash with 50 mL of heptane. Dry in a vacuum oven at 50° C. for 5 hours and obtain 3.6 g of diethyl-carbamic acid 2-(4-methoxy-phenyl)-3-[4-(2-piperidin-1-yl-ethoxy)-phenoxy]-benzo[b]thiophen-6-yl ester as a white solid. MS: [M+H]: 575.2.

Workup

  1. customTo a 500 mL flask (fitted with a stir bar)
  2. customto form a yellow solution
  3. customquench with 100 mL of EtOAc and 200 mL of 0.5 N NaOH
  4. customTransfer the mixture to a separation funnel, separate the organic layer
  5. washwash the organic layer with 100 mL of water and 50 mL of brine
  6. dry with materialDry over sodium sulfate
  7. concentrationconcentrate which
  8. customresults in a thick oil
  9. stirringStir the white slurry at room temperature overnight
  10. customCollect the white solid
  11. filtrationby filtration
  12. washwash with 50 mL of heptane
  13. customDry in a vacuum oven at 50° C. for 5 hours

Sources & evidence

ORD record
ord-e2981fad5a8e492a9548426f67c4c867
Source dataset
uspto-grants-2012_02
Patent number
US08124776B2

Reaction notes

Loading…