N,N-Dimethylaniline → HCID 86759014, compound

HRID 1826531Notes

Reaction equation

HRID 1826531 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:21]=[CH:22][CH:23]=1)[NH:6][C:7]1[N:8]=[C:9]([NH:17][C:18](=[O:20])[CH3:19])[NH:10][C:11](=O)[C:12]=1[N+:13]([O-:15])=[O:14])#[N:2].CN(C)C1C=CC=CC=1.P(Cl)(Cl)([Cl:35])=O>C(#N)C.[Cl-].C([N+](CC)(CC)CC)C>[Cl:35][C:11]1[C:12]([N+:13]([O-:15])=[O:14])=[C:7]([NH:6][C:5]2[CH:21]=[CH:22][CH:23]=[C:3]([C:1]#[N:2])[CH:4]=2)[N:8]=[C:9]([NH:17][C:18](=[O:20])[CH3:19])[N:10]=1

Participants

6

Reactant 3

HCID 949N,N-DimethylanilineHCID 24813Phosphorus oxychlorideHCID 136388349HCID 136388349, compound

Product 1

HCID 86759014HCID 86759014, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 5946Tetraethylammonium ChlorideCatalystHCID 6342AcetonitrileSolvent

Procedure

N1-[4-(3-Cyanoanilino)-5-nitro-6-oxo-1,6-dihydro-2-pyrimidinyl]acetamide (2.5 g) was suspended in 50 ml of acetonitrile, then 2.64 g of tetraethylammonium chloride, 1 ml of N,N-dimethylaniline and 4.5 ml of phosphorus oxy-chloride were added and the mixture was heated under reflux for 5 hours. The reaction solution was returned to room temperature and added to ice-water and the mixture was stirred for 30 minutes. The resulting crystals were collected by filtration washed with water and dried to give 2.5 g of N1-[4-chloro-6-(3-cyanoanilino)-5-nitro-2-pyrimidinyl]acetamide. The yield was 93%.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 5 hours
  3. customwas returned to room temperature
  4. filtrationThe resulting crystals were collected by filtration
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-52ae0c18599c4b9f9f2df0603d327aea
Source dataset
uspto-grants-2006_05
Patent number
USRE039112E1

Reaction notes

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