Sodium dicyanamide → HCID 178422094, compound

HRID 855947Notes

Reaction equation

HRID 855947 reaction equation
Cl.[I:2][C:3]1[CH:4]=[C:5]([NH2:13])[CH:6]=[C:7]2[C:11]=1[NH:10][C:9]([CH3:12])=[CH:8]2.[N-:14]([C:17]#[N:18])[C:15]#[N:16].[Na+]>CN(C)C=O>[C:15]([N:14]=[C:17]([NH2:18])[NH:13][C:5]1[CH:6]=[C:7]2[C:11](=[C:3]([I:2])[CH:4]=1)[NH:10][C:9]([CH3:12])=[CH:8]2)#[N:16]

Participants

4

Reactant 2

HCID 4350929Sodium dicyanamideHCID 86595125HCID 86595125, compound

Product 1

HCID 178422094HCID 178422094, compoundYield 42.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
45 °C

Procedure

A solution of 7-iodo-2-methyl-1H-indol-5-ylamine hydrochloride XVII (1.9 g, 6.158 mmol) in N,N-dimethylformamide (30 mL) at 25° C. was treated with sodium dicyanamide (1.37 g, 15.397 mmol) and then warmed to 45° C. for 4 h. The resulting mixture filtered and concentrated in vacuo and the residue treated with water (20 mL). The resulting mixture was allowed to stand at 25° C. for 2.5 h during which time a solid formed. The solid was collected by filtration and washed with water, resuspended in methanol, filtered and dried to give N″-cyano-N-(7-iodo-2-methyl-1H-indol-5-yl)guanidine XVIII (0.88 g, 42%) as a light grey solid: LRMS for C11H10IN5 (M−H)+ at m/z=338.

Workup

  1. filtrationThe resulting mixture filtered
  2. concentrationconcentrated in vacuo
  3. additionthe residue treated with water (20 mL)
  4. customa solid formed
  5. filtrationThe solid was collected by filtration
  6. washwashed with water
  7. filtrationfiltered
  8. customdried

Sources & evidence

ORD record
ord-871e957e3ca84f49930fa37d7a339a73
Source dataset
uspto-grants-2007_08
Patent number
US07262297B2

Reaction notes

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