Chlorosuccinimide → HCID 20477716, compound

HRID 904833Notes

Reaction equation

HRID 904833 reaction equation
S1C=CC=CN1N1C2C=C(C(=C)C3C=CC=CC=3)C=CC=2N=C1N.ClN1C(=O)CCC1=O.Cl.[S:34]1[CH:39]=[CH:38][CH:37]=[CH:36][N:35]1[N:40]1[C:44]2[CH:45]=[C:46]([C:49](=[C:56]([Cl:58])[Cl:57])[C:50]3[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=3)[CH:47]=[CH:48][C:43]=2[N:42]=[C:41]1[NH2:59]>O1CCCC1>[S:34]1[CH:39]=[CH:38][CH:37]=[CH:36][N:35]1[N:40]1[C:44]2[CH:45]=[C:46]([C:49](=[C:56]([Cl:58])[Cl:57])[C:50]3[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=3)[CH:47]=[CH:48][C:43]=2[N:42]=[C:41]1[NH2:59]

Participants

5

Reactant 3

HCID 31398ChlorosuccinimideHCID 20477715HCID 20477715, compoundHCID 20477732HCID 20477732, compound

Product 1

HCID 20477716HCID 20477716, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1.0 g of 1-(thiazin-2-yl)-2-amino-6-(α-methylenebenzyl)benzimidazole in 50 ml. of tetrahydrofuran containing 500 mg. of N-chlorosuccinimide stood at room temperature for twelve hours. A small amount of solid precipitate was removed by filtration. An additional 500 mg. portion of N-chlorosuccinimide was added to the filtrate and the solution was stirred for six hours at room temperature. Another 500 mg. portion of N-chlorosuccinimide was then added to the reaction mixture and stirring was continued for twelve hours. The white precipitate which had formed was collected by filtration and air dried to give 640 mg. (57%) of 1-(thiazin-2-yl)-2-amino-6-(α-dichloromethylenebenzyl)benzimidazole hydrochloride. M.P. 214°-217° C.

Workup

  1. customA small amount of solid precipitate was removed by filtration
  2. additionportion of N-chlorosuccinimide was added to the filtrate
  3. additionportion of N-chlorosuccinimide was then added to the reaction mixture
  4. stirringstirring
  5. waitwas continued for twelve hours
  6. customThe white precipitate which had formed
  7. filtrationwas collected by filtration and air
  8. customdried
  9. customto give 640 mg

Sources & evidence

ORD record
ord-178e81cbbb4f43ab9b2dfbb3251c0399
Source dataset
uspto-grants-1983_12
Patent number
US04420479

Reaction notes

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