Sodium Carbonate → HCID 58088955, compound

HRID 2099221Notes

Reaction equation

HRID 2099221 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:11]=[CH:12][C:13]=1[CH3:14])[C:5]([NH:7][CH:8]1[CH2:10][CH2:9]1)=[O:6].[N:15]([O-])=O.[Na+].[Sn](Cl)Cl.C([O-])([O-])=O.[Na+].[Na+]>O.Cl>[CH:8]1([NH:7][C:5](=[O:6])[C:4]2[CH:11]=[CH:12][C:13]([CH3:14])=[C:2]([NH:1][NH2:15])[CH:3]=2)[CH2:9][CH2:10]1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 24479Stannous ChlorideHCID 119838543-amino-N-cyclopropyl-4-methylbenzamideHCID 23668193Sodium Nitrite

Product 1

HCID 58088955HCID 58088955, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolvent2×HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 3-Amino-N-cyclopropyl-4-methyl-benzamide (52 mg, 0.27 mmol) in water (3 ml) at 0° C. was added conc. HCl (3 mL) followed by the addition of sodium nitrite (20 mg, 0.30 mmol). The reaction mixture was stirred at 0° C. for 40 min then a solution of tin(II)chloride (114 mg, 0.61 mmol) in conc. HCl (1 mL) was added and the mixture was stirred for 1 hr then allowed to stand at −20° C. for 20 hr before it was warmed to RT. It was neutralized with Na2CO3 solution and extracted with CH2Cl2 six times. The combined extracts were dried over Na2SO4, concentrated, and the resulting solid was used without further purification. HPLC tR 1.06 min; MS m/z 205.9 [M+H]+.

Workup

  1. stirringthe mixture was stirred for 1 hr
  2. waitto stand at −20° C. for 20 hr before it
  3. temperaturewas warmed to RT
  4. extractionextracted with CH2Cl2 six times
  5. dry with materialThe combined extracts were dried over Na2SO4
  6. concentrationconcentrated
  7. customthe resulting solid was used without further purification

Sources & evidence

ORD record
ord-f9fd6ebfaac945ff895af61f94c4c0d3
Source dataset
uspto-grants-2009_08
Patent number
US07569571B2

Reaction notes

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