Methylamine → HCID 68704053, compound

HRID 2242859Notes

Reaction equation

HRID 2242859 reaction equation
[Cl:1][C:2]1[N:3]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19]Cl)=[CH:13][CH:12]=2)[N:4]=[C:5]2[C:10]=1[CH:9]=[CH:8][CH:7]=[CH:6]2.[CH3:21][NH2:22]>C(#N)C>[ClH:1].[Cl:1][C:2]1[N:3]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][NH:22][CH3:21])=[CH:13][CH:12]=2)[N:4]=[C:5]2[C:10]=1[CH:9]=[CH:8][CH:7]=[CH:6]2

Participants

4

Reactant 2

HCID 6329MethylamineHCID 58900138HCID 58900138, compound

Product 1

HCID 68704053HCID 68704053, compoundYield 179.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of the product from Step 1 (0.1 g, 0.33 mmol), methylamine (40% in water, 3 mL, 81 mmol) in acetonitrile (2 mL) was heated to 60° C. for 7 h, and then room temperature for 16 h. The mixture was extracted with ethyl acetate. The combined organic portions were acidified with 10% HCl to pH to 1, and stirred at 0° C. for 1 h. The product was collected on a filter, washed with 1N HCl, water and hexane. After dried under vacuum, the title compound (100 mg, 91%) was obtained as hydrochloride salt; MS (APCI) m/z 302 (M+1, 100).

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. customThe product was collected on a filter
  3. washwashed with 1N HCl, water and hexane
  4. customAfter dried under vacuum

Sources & evidence

ORD record
ord-e86f90d042494b86ab5d8296abd327e0
Source dataset
uspto-grants-2010_03
Patent number
US07674802B2

Reaction notes

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