Acetonitrile → HCID 86649698, compound

HRID 2060765Notes

Reaction equation

HRID 2060765 reaction equation
[CH3:1][S:2]([O:5][CH2:6][CH:7]1[C:12]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([Br:19])[CH:14]=2)=[CH:11][CH2:10][O:9][CH2:8]1)(=[O:4])=[O:3].[NH2:20][C:21]([NH2:23])=[S:22].C(#N)C>C(O)(C)C>[CH3:1][S:2]([OH:5])(=[O:4])=[O:3].[C:21]([S:22][CH2:6][CH:7]1[C:12]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([Br:19])[CH:14]=2)=[CH:11][CH2:10][O:9][CH2:8]1)(=[NH:20])[NH2:23]

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 2723790ThioureaHCID 57475771HCID 57475771, compound

Product 1

HCID 86649698HCID 86649698, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of (4-(3-bromophenyl)-3,6-dihydro-2H-pyran-3-yl)methyl methanesulfonate (4.82 g, 11.7 mmol) and thiourea (1.78 g, 23.3 mmol) in isopropyl alcohol (100 mL) is heated to reflux for 24 h. The reaction is cooled and the solvent is removed under reduced vacuum to give a residue that is combined with acetonitrile (30 mL) and hexanes (10 mL). A solid crystallizes and the slurry is cooled to 0° C. The slurry is filtered using 3:1 ACN:hexanes as a rinse (25 mL) to give the title compound as the mesylate salt (3.45 g, 70%). ES/MS m/e (79Br/81Br) 327, 329 (M+1).

Workup

  1. temperatureis heated
  2. temperatureto reflux for 24 h
  3. temperatureThe reaction is cooled
  4. customthe solvent is removed under reduced vacuum
  5. customto give a residue that
  6. customA solid crystallizes
  7. filtrationThe slurry is filtered
  8. washhexanes as a rinse (25 mL)

Sources & evidence

ORD record
ord-8e8841837e4c43138112f98b23f7cde0
Source dataset
uspto-grants-2012_10
Patent number
US08278441B2

Reaction notes

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