Methanesulfonic Acid → HCID 18536348, compound

HRID 412624Notes

Reaction equation

HRID 412624 reaction equation
[Cl:1][CH2:2][C:3]#[N:4].C[O-].[Na+].CS(O)(=O)=O.N[C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][C:21]=1[NH:22][CH2:23][C:24](=[O:32])[NH:25][CH:26]1[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1)[C:17]#[N:18]>CO.O>[Cl:1][CH2:2][C:3]1[N:22]([CH2:23][C:24](=[O:32])[NH:25][CH:26]2[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31]2)[C:21]2[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[CH:15][C:14]=2[N:4]=1

Participants

7

Reactant 4

HCID 6395Methanesulfonic AcidHCID 7856ChloroacetonitrileHCID 10942334Sodium MethoxideHCID 18536365HCID 18536365, compound

Product 1

HCID 18536348HCID 18536348, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of chloroacetonitrile (3.9 ml) in methanol (166 ml) was added sodium methoxide (3.29 g), and the mixture was stirred at room temperature for 40 min under a nitrogen atmosphere. Methanesulfonic acid (7.91 ml) and 3-amino4-(cyclohexylcarbamoylmethylamino)benzonitrile (8.3 g) were added, and the mixture was stirred for 3 hours. After completion of the reaction, water (166 ml) was added and the precipitated solid was collected by filtration, and washed with a small amount of water. The obtained solid was stirred in a mixture of hexane and tetrahydrofuran, collected by filtration and dried under reduced pressure to give the title compound (9.30 g).

Workup

  1. stirringthe mixture was stirred for 3 hours
  2. additionwas added
  3. filtrationthe precipitated solid was collected by filtration
  4. washwashed with a small amount of water
  5. stirringThe obtained solid was stirred in a mixture of hexane and tetrahydrofuran
  6. filtrationcollected by filtration
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-da922c1501f6417ab111fb8b0bcc272f
Source dataset
uspto-grants-2003_05
Patent number
US06562828B1

Reaction notes

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