Sodium dicyanamide → HCID 178512364, compound

HRID 1765024Notes

Reaction equation

HRID 1765024 reaction equation
Cl.[I:2][C:3]1[CH:4]=[C:5]([NH2:12])[CH:6]=[C:7]2[C:11]=1[NH:10][CH:9]=[CH:8]2.[N-:13]([C:16]#[N:17])[C:14]#[N:15].[Na+]>CN(C)C=O>[C:14]([N:13]=[C:16]([NH2:17])[NH:12][C:5]1[CH:6]=[C:7]2[C:11](=[C:3]([I:2])[CH:4]=1)[NH:10][CH:9]=[CH:8]2)#[N:15]

Participants

4

Reactant 2

HCID 4350929Sodium dicyanamideHCID 21106349HCID 21106349, compound

Product 1

HCID 178512364HCID 178512364, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 7-iodo-1H-indol-5-ylamine hydrochloride IV (24.6 g, 83.7 mmol) in N,N-dimethylformamide (400 mL) at 25° C. was treated with sodium dicyanamide (18.6 g, 209 mmol). The reaction mixture was warmed to 50° C. for 2 h, concentrated in vacuo, and the residue treated with water (500 mL). The resulting mixture was allowed to stand at 25° C. for 2.5 h during which time a yellow precipitate formed. The precipitate was collected by filtration and washed with water to afford N″-cyano-N-(7-iodo-1H-indol-5-yl)guanidine V (22.59 g, 83%) as a light yellow solid: 1H NMR (DMSO-d6, 300 MHz) δ 11.02 (broad s, 1H), 8.89 (broad s, 1H), 7.46 (d, J=1.83 Hz, 1H), 7.37 (d, J=1.83 Hz, 1H), 7.35 (t, J=2.56 Hz, 1H), 6.85 (broad s, 2H), 6.56 (dd, J1=1.83 Hz, J2=3.10 Hz, 1H).

Workup

  1. concentrationconcentrated in vacuo
  2. additionthe residue treated with water (500 mL)
  3. customa yellow precipitate formed
  4. filtrationThe precipitate was collected by filtration
  5. washwashed with water

Sources & evidence

ORD record
ord-94a1ec50df984518a69f1ece9637a67b
Source dataset
uspto-grants-2007_06
Patent number
US07226915B2

Reaction notes

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