Sodium Cyanate → 4-(4-isopropyl-phenyl)-1-(3-nitro-benzyl)-6-propargyloxy-1H-quinazolin-2-one

HRID 445173Notes

Reaction equation

HRID 445173 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]([C:12]2[CH:17]=[C:16]([O:18][CH2:19][C:20]#[CH:21])[CH:15]=[CH:14][C:13]=2[NH:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([N+:30]([O-:32])=[O:31])[CH:25]=2)=O)=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[O-:33][C:34]#[N:35].[Na+]>C(O)(=O)C.O>[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:12]3[C:13](=[CH:14][CH:15]=[C:16]([O:18][CH2:19][C:20]#[CH:21])[CH:17]=3)[N:22]([CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([N+:30]([O-:32])=[O:31])[CH:25]=3)[C:34](=[O:33])[N:35]=2)=[CH:6][CH:5]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 517096Sodium CyanateHCID 86761896(4-Isopropyl-phenyl)-[2-(3-nitro-benzylamino)-5-propargyloxy-phenyl]-methanone

Product 1

HCID 451416224-(4-isopropyl-phenyl)-1-(3-nitro-benzyl)-6-propargyloxy-1H-quinazolin-2-one

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A red solution of 34 g (79.4 mmol) of the benzophenone prepared in step A in 200 ml acetic acid is treated with 6.2 g (95 mmol) sodium cyanate under vigorous stirring which is continued overnight. The mixture is diluted with water and extracted with ethyl acetate. Concentration after washing with bicarbonate solution yields several crops of product. While the initial batches are yellow and pure, the subsequent ones are orange and have to be purified by flash chromatography. Combined yield: 25.9 g (72%). m.p. 167-168° C.

Workup

  1. extractionextracted with ethyl acetate
  2. concentrationConcentration
  3. washafter washing with bicarbonate solution
  4. customyields several crops of product
  5. customto be purified by flash chromatography

Sources & evidence

ORD record
ord-e7536eb2431f425191c990a30a375852
Source dataset
uspto-grants-2013_07
Patent number
US08476286B2

Reaction notes

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