Phenyl isocyanate → HCID 71621927, compound

HRID 871024Notes

Reaction equation

HRID 871024 reaction equation
[NH2:1][C:2]1[S:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([NH2:13])[CH:8]=2)[C:3]=1[C:14]([NH2:16])=[O:15].C(N(CC)C(C)C)(C)C.[C:26]1([N:32]=[C:33]=[O:34])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>O1CCOCC1>[NH2:1][C:2]1[S:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([NH:13][C:33]([NH:32][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[O:34])[CH:8]=2)[C:3]=1[C:14]([NH2:16])=[O:15]

Participants

5

Reactant 3

HCID 7672Phenyl isocyanateHCID 81531DiisopropylethylamineHCID 86689233HCID 86689233, compound

Product 1

HCID 71621927HCID 71621927, compoundYield 97.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 5-amino-3-(3-aminophenyl)isothiazole-4-carboxamide (21 mg, 0.090 mmol), N,N-diisopropylethylamine (0.039 mL, 0.23 mmol), and phenyl isocyanate (0.014 mL, 0.13 mmol) in 1.0 mL dioxane was reacted at rt for 1 hour. The precipitant was filtered and rinsed with 30% EtOAc/hexane to give the title compound as a white solid (31 mg, 96%).

Workup

  1. customwas reacted at rt for 1 hour
  2. filtrationThe precipitant was filtered
  3. washrinsed with 30% EtOAc/hexane

Sources & evidence

ORD record
ord-22d49e9bac96422aa6317b5bdee72e2c
Source dataset
uspto-grants-2015_03
Patent number
US08969583B2

Reaction notes

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