N,N-Diethylaniline → 2-(4-tert-butylphenyl)-7-chloro-6-nitro-5H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-5-one

HRID 1906528Notes

Reaction equation

HRID 1906528 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[S:24][C:14]3=[N:15][C:16](O)=[C:17]([N+:20]([O-:22])=[O:21])[C:18](=[O:19])[N:13]3[N:12]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].P(Cl)(Cl)([Cl:27])=O.CCN(C1C=CC=CC=1)CC>>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[S:24][C:14]3=[N:15][C:16]([Cl:27])=[C:17]([N+:20]([O-:22])=[O:21])[C:18](=[O:19])[N:13]3[N:12]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 7061N,N-DiethylanilineHCID 24813Phosphorus oxychlorideHCID 1358024512-(4-tert-butylphenyl)-7-hydroxy-6-nitro-5H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-5-one

Product 1

HCID 135918342-(4-tert-butylphenyl)-7-chloro-6-nitro-5H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-5-one

Procedure

6.0 g of 2-(4-tert-butylphenyl)-7-hydroxy-6-nitro-5H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-5-one was added to a mixture of 25 ml of phosphorus oxychloride and 4 ml of diethylaniline, and the resulting mixture was heated at a temperature of 70° to 80° C. for 2 hours. After cooling, the precipitate formed was filtered, washed successively with water, isopropanol and diethyl ether to obtain 4.3 g of 2-(4-tert-butylphenyl)-7-chloro-6-nitro-5H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-5-one as crystals having a melting point of 245° to 248° C.

Workup

  1. temperaturethe resulting mixture was heated at a temperature of 70° to 80° C. for 2 hours
  2. temperatureAfter cooling
  3. customthe precipitate formed
  4. filtrationwas filtered
  5. washwashed successively with water, isopropanol and diethyl ether

Sources & evidence

ORD record
ord-3bee438ad1ee4bb59939b956547740ef
Source dataset
uspto-grants-1987_03
Patent number
US04652646

Reaction notes

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