Chlorosuccinimide → HCID 19811540, compound

HRID 373246Notes

Reaction equation

HRID 373246 reaction equation
[Cl:1][C:2]1[N:7]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[C:21]3[N:25]([C:26]([C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=4)([C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)[C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[N:24]=[N:23][N:22]=3)=[CH:11][CH:10]=2)[C:6](=[O:45])[N:5]([CH2:46][CH2:47][CH3:48])[C:4](=[O:49])[CH:3]=1.[Cl:50]N1C(=O)CCC1=O>C(Cl)(Cl)Cl>[Cl:50][C:3]1[C:4](=[O:49])[N:5]([CH2:46][CH2:47][CH3:48])[C:6](=[O:45])[N:7]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[C:21]3[N:25]([C:26]([C:33]4[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=4)([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[C:39]4[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=4)[N:24]=[N:23][N:22]=3)=[CH:11][CH:10]=2)[C:2]=1[Cl:1]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 198115276-Chloro-3-propyl-1-[[2'-(N-trityltetrazol-5-yl)-biphenyl-4-yl]methyl]pyrimidine-2,4(1H,3H)-dione

Product 1

HCID 19811540HCID 19811540, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 6-chloro-3-propyl-1-[[2'-(N-trityltetrazol-5-yl)biphenyl-4-yl]methyl]pyrimidine-2,4(1H,3H)-dione (0.6 g) and N-chlorosuccinimide (0.14 g) in chloroform (10 ml) was heated under reflux for 18 hours. The reaction mixture concentrated to dryness and the resulting residue was purified by column chromatography on silica gel to give colorless amorphous powders (0.22 g, 35%).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 18 hours
  3. concentrationThe reaction mixture concentrated to dryness
  4. customthe resulting residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-8f627d80ea6543f09b59598c756c1fb0
Source dataset
uspto-grants-1992_11
Patent number
US05162326

Reaction notes

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