Diphenyl N-Cyanocarbonimidate → HCID 178512287, compound

HRID 260168Notes

Reaction equation

HRID 260168 reaction equation
[N:1]([C:4]1[CH:5]=[C:6]([CH:8]=[C:9]([I:11])[CH:10]=1)[NH2:7])=[N+:2]=[N-:3].[CH:12]1[CH:17]=[CH:16][C:15]([O:18][C:19](OC2C=CC=CC=2)=[N:20][C:21]#[N:22])=[CH:14][CH:13]=1>C(Cl)(Cl)Cl>[N:1]([C:4]1[CH:5]=[C:6]([NH:7][C:19](=[N:20][C:21]#[N:22])[O:18][C:15]2[CH:16]=[CH:17][CH:12]=[CH:13][CH:14]=2)[CH:8]=[C:9]([I:11])[CH:10]=1)=[N+:2]=[N-:3]

Participants

4

Reactant 2

HCID 688090Diphenyl N-CyanocarbonimidateHCID 22402759HCID 22402759, compound

Product 1

HCID 178512287HCID 178512287, compoundYield 94.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

CHART B, Step B-1. To a solution of 3-azido-5-iodoaniline (A-4, 2.42 g, 9.31 mmol) in chloroform (8 mL) is added diphenyl cyanocarbonimidate (2.21g, 9.31 mmol). The solvent is allowed to evaporate at a temperature of 70° C. overnight. The resulting solid is washed with ether, filtered and dried to afford 3.558 g of N-(3-azido-5-iodophenyl)-N'-cyanocarbamimidic acid, phenyl ester (B-1) which is used without further purification. A small analytical sample is recrystallized from ethyl acetate in hexane. Mp=195° C. (dec). IR (mull) 3094, 3078, 2954, 2925, 2867, 2854, 2208, 2121, 2106, 1652, 1600, 1590, 1565, 1504, 1491, 1446, 1433, 1401, 1302, 1219, 1195, 833 cm -1 ; 1H NMR (DMSO) δ10.57 (bs (1 H), 7.50 (t, 1 H, J=2 Hz), 7.28 (m, 2 H), 7.10 (m, 5 H); 13C NMR (DMSO) δ151.4, 141.3, 138.6, 129.9, 128.2, 126.4, 124.6, 120.8, 113.6, 95.0; Mass Spec (70eV, EI) m/z 404 (parent), 376, 249 (base), 222, 207, 194, 155, 145, 128, 118, 103, 94, 77, 65, 51; Exact mass calculated for C14H9IN6O: 403.9884. Found: 403.9877. Melt solvate: 3.6% ethyl acetate; Analysis calculated for C14H9IN6O plus 3.6% C4H8O2 : C, 42.07; H, 2.49; N, 20.04; Found; C, 41.95; H, 2.25; N, 19.76.

Workup

  1. customto evaporate at a temperature of 70° C. overnight
  2. washThe resulting solid is washed with ether
  3. filtrationfiltered
  4. customdried

Sources & evidence

ORD record
ord-72e314c03d5f4ca3be15e1deb0025278
Source dataset
uspto-grants-1996_06
Patent number
US05525742

Reaction notes

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