Potassium Hydroxide → HCID 68958984, compound

HRID 1423892Notes

Reaction equation

HRID 1423892 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([CH:6]=[O:7])=[CH:2]1.[OH-].[K+].[N+:10]([CH2:12][C:13]([N:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1)=[O:14])#[C-:11]>CO>[S:1]1[CH:5]=[CH:4][C:3]([C@@H:6]2[O:7][CH:11]=[N:10][C@H:12]2[C:13]([N:15]2[CH2:16][CH2:17][O:18][CH2:19][CH2:20]2)=[O:14])=[CH:2]1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 681353-ThiophenecarboxaldehydeHCID 6455475Morpholine, 4-(isocyanoacetyl)-2×

Product 1

HCID 68958984HCID 68958984, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

SLA 09052A was prepared in accordance with method D using thiophene-3-carbaldehyde (0.768 mL, 5.35 mmol), KOH (0.273 mg, 4.86 mmol) in methanol (5 mL) and 2-isocyano-1-morpholinoethanone SLA 07118 (0.75 g, 4.86 mmol). The solution was stirred for 2 h at 0° C. After work-up the residue was purified by column chromatography (florisil, EtOAc). After evaporation and drying, trans-(4,5-dihydro-5-(thiophen-3-yl)oxazol-4-yl)(morpholino)methanone SLA 09052A (0.327 g, 25% yield) was obtained as a yellow oil.

Workup

  1. customSLA 09052A was prepared in accordance with method D
  2. customAfter work-up the residue was purified by column chromatography (florisil, EtOAc)
  3. customAfter evaporation
  4. customdrying

Sources & evidence

ORD record
ord-b22cbc13c5c641ce8727ff8a5cc2bd09
Source dataset
uspto-grants-2015_01
Patent number
US08927589B2

Reaction notes

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