Chlorosuccinimide → HCID 178448725, compound

HRID 979647Notes

Reaction equation

HRID 979647 reaction equation
[CH2:1]([N:5]1[C:14](=[NH:15])[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:18][CH3:19])[C:12]=2[O:16][CH3:17])[NH:7][C:6]1=[O:20])[CH2:2][CH2:3][CH3:4].[Cl:21]N1C(=O)CCC1=O>C(Cl)(Cl)Cl>[CH2:1]([N:5]1[C:14](=[NH:15])[C:13]2[C:8](=[C:9]([Cl:21])[CH:10]=[C:11]([O:18][CH3:19])[C:12]=2[O:16][CH3:17])[NH:7][C:6]1=[O:20])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 178448724HCID 178448724, compound

Product 1

HCID 178448725HCID 178448725, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 0.5 g (1.77 mmol) of 3-butyl-5,6-dimethoxy-4-imino-2(1H)quinazolinone and N-chlorosuccinimide (0.45 g, 3.35 mmol) in 100 ml of CHCl3 was heated at reflux for 18 hours. The reaction mixture was cooled, washed with 10% aqueous sodium thiosulfate (3×35 ml), dried with anhydrous MgSO4 and evaporated to give the crude product as an orange-brown solid. Recrystallization from 2-propanol afforded the desired product in analytical purity; yield 0.30 g (54.5%) mp 155°-157°.

Workup

  1. temperatureat reflux for 18 hours
  2. temperatureThe reaction mixture was cooled
  3. washwashed with 10% aqueous sodium thiosulfate (3×35 ml)
  4. dry with materialdried with anhydrous MgSO4
  5. customevaporated
  6. customto give the crude product as an orange-brown solid
  7. customRecrystallization from 2-propanol

Sources & evidence

ORD record
ord-2b7cb07269ac45668d7b1101c2322030
Source dataset
uspto-grants-1987_05
Patent number
US04668787

Reaction notes

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