HCID 11372145, compound → HCID 11427849, compound

HRID 1592065Notes

Reaction equation

HRID 1592065 reaction equation
[NH2:1][C:2]1[C:3]2[S:10][C:9]3[N:11]=[C:12]([N:18]4[CH2:23][CH2:22][CH:21]([NH:24]C=O)[CH2:20][CH2:19]4)[CH:13]=[C:14]([CH2:15][CH2:16][CH3:17])[C:8]=3[C:4]=2[N:5]=[CH:6][N:7]=1>Cl.O.C(=O)([O-])[O-].[Na+].[Na+]>[NH2:24][CH:21]1[CH2:22][CH2:23][N:18]([C:12]2[CH:13]=[C:14]([CH2:15][CH2:16][CH3:17])[C:8]3[C:4]4[N:5]=[CH:6][N:7]=[C:2]([NH2:1])[C:3]=4[S:10][C:9]=3[N:11]=2)[CH2:19][CH2:20]1

Participants

5

Reactant 1

HCID 11372145HCID 11372145, compound

Product 1

HCID 11427849HCID 11427849, compoundYield 43%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 10340Sodium CarbonateSolvent

Conditions

Temperature
60 °C

Procedure

The above formamide (249 mg, 0.672 mmol) was dissolved in 1 mL of concentrated HCl and 1 mL of water. The reaction mixture was heated in a SmithSynthesizer™ (Personal Chemistry) at 60° C. for 1 h. The solvent was removed in vacuo. The residue was recrystallized from MeOH to give a yellow solid. The solid was stirred in 5 mL of 2 M sodium carbonate solution for 6 h. The resulting yellow solid was collected by filtration, washed with water and air dried to provide the title compound (98 mg, 43%).

Workup

  1. customThe solvent was removed in vacuo
  2. customThe residue was recrystallized from MeOH
  3. customto give a yellow solid
  4. filtrationThe resulting yellow solid was collected by filtration
  5. washwashed with water and air
  6. customdried

Sources & evidence

ORD record
ord-ee7b6532928e476eb51d54bcf82aae53
Source dataset
uspto-grants-2007_11
Patent number
US07291733B2

Reaction notes

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