Hydrochloric Acid → HCID 118272043, compound

HRID 590776Notes

Reaction equation

HRID 590776 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([NH2:12])[CH2:9][O:10][CH3:11])=[CH:4][CH:3]=1.Cl.[O-:14][C:15]#[N:16].[K+].C(=O)(O)[O-].[Na+]>O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([NH:12][C:15]([NH2:16])=[O:14])[CH2:9][O:10][CH3:11])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 11378442Potassium cyanateHCID 167942011-(4-fluorophenyl)-2-methoxyethan- 1-amine

Product 1

HCID 118272043HCID 118272043, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

To a microwave vial equipped with a stir bar was added 1-(4-fluorophenyl)-2-methoxyethanamine (1.2 g, 7.09 mmol) and water (10 mL). To this mixture was added HCl (1N, 7.23 mL, 7.23 mmol) and potassium cyanate (2.88 g, 35.5 mmol). The mixture was heated in a microwave reactor to 80° C. for 1 h. Saturated sodium bicarbonate was added and the products extracted into EtOAc (×4). The organic layers were combined, washed with brine (×2), and dried over MgSO4. The material was concentrated in vacuo while loading onto silica gel. Purification by flash chromatography (0-10% EtOAc-Hexanes) gave 1-(1-(4-fluorophenyl)-2-methoxyethyl)urea. MS ESI calc'd. for C10H13FN2O2 [M+1]+ 213. found 213.

Workup

  1. customTo a microwave vial equipped with a stir bar
  2. extractionthe products extracted into EtOAc (×4)
  3. washwashed with brine (×2)
  4. dry with materialdried over MgSO4
  5. concentrationThe material was concentrated in vacuo
  6. customPurification by flash chromatography (0-10% EtOAc-Hexanes)

Sources & evidence

ORD record
ord-b753816701694aad80e1c7022d6c191c
Source dataset
uspto-grants-2016_01
Patent number
US09233979B2

Reaction notes

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