HCID 12803100, compound → HCID 12803105, compound

HRID 1381547Notes

Reaction equation

HRID 1381547 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:11][C:12]#[N:13].[O:14]([C:16]#[N:17])[K]>CC(O)=O.O>[C:12]([CH2:11][C:5]1[C:4]2[C:8](=[CH:9][CH:10]=[C:2]([NH:1][C:16]([NH2:17])=[O:14])[CH:3]=2)[NH:7][CH:6]=1)#[N:13]

Participants

5

Reactant 2

HCID 12803100HCID 12803100, compoundHCID 178418250HCID 178418250, compound

Product 1

HCID 12803105HCID 12803105, compoundYield 53%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

To a solution of 21.3 g (0.124 mole) of 5-aminoindole-3-acetonitrile in 400 ml of 25% aq HOAc cooled to 0° was added 10.5 g (0.13 mole) of KOCN in 30 ml of H2O. The reaction mixture was stored at 0° for 14 hours after which a beige solid was filtered and recrystallized from methanol to give 14.0 g (53% yield) of N-(3-cyanomethyl-1H-indol-5-yl)urea. Further recrystallization affords an analytical sample: m.p. 219°-220°; i.r. (Nujol) 3455, 3300, 2250 and 1650 cm-1 ; nmr (d6 -DMSO) δ(TMS) 11.06 (1,S,indole NH ), 8.46 (1,S, --NHCO--), 7.70 (1,d,Jmeta =2 Hz), 7.37 (1,d,Jortho =9 Hz), 7.30 (1,S,indole C2H), 7.18 (1,d of d,Jortho =9 Hz, Jmeta =2 Hz), 5.73 (2,S,--CONH2) and 4.00 ppm (2,S,--CH2CN).

Workup

  1. filtrationafter which a beige solid was filtered
  2. customrecrystallized from methanol

Sources & evidence

ORD record
ord-974bcd878e9f493098d09e889e2f6392
Source dataset
uspto-grants-1989_02
Patent number
US04803218

Reaction notes

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