Diphenyl N-Cyanocarbonimidate → HCID 178512269, compound

HRID 260163Notes

Reaction equation

HRID 260163 reaction equation
[N:1]([C:4]1[CH:5]=[C:6]([CH:8]=[C:9]([Cl: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]([Cl:11])[CH:10]=1)=[N+:2]=[N-:3]

Participants

4

Reactant 2

HCID 688090Diphenyl N-CyanocarbonimidateHCID 224027643-Azido-5-chloroaniline

Product 1

HCID 178512269HCID 178512269, compoundYield 61.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Chart B, Step B-1. To a stirred solution of 3-azido-5-chloroaniline (A-4, 0.706 g, 4.18 mmol) in 6 mL of chloroform, is added diphenyl cyanocarbonimidate (0.997 g, 4.18 mmol). The solvent is allowed to evaporate at a temperature of 75° C. overnight. The resulting solid is triturated with ether and filtered. The solid is recrystallized from ethyl acetate/hexane to afford 0.808 g of N-(3-azido-5-chlorophenyl)-N'-cyanocarbamimidic acid, phenyl ester. (B-1) Mp 193°-194° C. (dec); IR (mull) 3084, 2954, 2925, 2210, 2117, 2104, 1652, 1608, 1581, 1500, 1449, 1438, 1405, 1222, 1197, 1002, 892 cm-1 ; 1H NMR (DMSO) δ10.9 (bs, 1 H), 7.45-7.20 (bm, 8 H), 7.07 (bs, 1 H); 13C NMR (DMSO) δ151.3, 141.5, 138.6, 134.0, 129.8, 126.4, 120.8, 119.4, 116.2, 112.8, 112.5; Analysis calculated for C14H9ClN6O: C, 53.77; H, 2.90; N, 26.87; Cl, 11.34. Found: C, 53.39; H, 2.71; N, 26.54; Cl, 11.32.

Workup

  1. customto evaporate at a temperature of 75° C. overnight
  2. customThe resulting solid is triturated with ether
  3. filtrationfiltered
  4. customThe solid is recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-529d842831e647fcaec5358028c6cadb
Source dataset
uspto-grants-1996_06
Patent number
US05525742

Reaction notes

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