HCID 12069124, compound → HCID 21487220, compound

HRID 1414379Notes

Reaction equation

HRID 1414379 reaction equation
Cl[C:2]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([O-:10])=[O:9])=[C:6](C2C=CC=CC=2)[CH:5]=1)=O.[NH2:19][C:20]1[CH:25]=[C:24]([NH:26][S:27]([C:30]2[CH:35]=[CH:34][C:33]([CH3:36])=[CH:32][CH:31]=2)(=[O:29])=[O:28])[C:23]([NH:37][S:38]([C:41]2[CH:46]=[CH:45][C:44]([CH3:47])=[CH:43][CH:42]=2)(=[O:40])=[O:39])=[CH:22][C:21]=1[NH2:48]>C1C(Cl)=CC=C(Cl)C=1>[C:8]([C:7]1[CH:6]=[CH:5][C:4]([C:2]2[NH:48][C:21]3[CH:22]=[C:23]([NH:37][S:38]([C:41]4[CH:46]=[CH:45][C:44]([CH3:47])=[CH:43][CH:42]=4)(=[O:40])=[O:39])[C:24]([NH:26][S:27]([C:30]4[CH:35]=[CH:34][C:33]([CH3:36])=[CH:32][CH:31]=4)(=[O:28])=[O:29])=[CH:25][C:20]=3[N:19]=2)=[CH:12][CH:11]=1)([O:10][C:4]1[CH:12]=[CH:11][CH:7]=[CH:6][CH:5]=1)=[O:9]

Participants

4

Reactant 2

HCID 12069124HCID 12069124, compoundHCID 131710586HCID 131710586, compound

Product 1

HCID 21487220HCID 21487220, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 46851,4-DichlorobenzeneSolvent

Procedure

To a solution containing 8.7 g (33.6mmole) of p-chlorocarbonylphenylbenzoate dissolved in 50 ml of dichlorobenzene was added 5 g (11.2 mmole) of 1,2-diamino-4,5-bis(p-toluenesulfonamido)benzene. The resulting mixture was heated to reflux under nitrogen (frothing), and was maintained at that temperature for 2 hours. The solution was then distilled to half of the original volume, and heptane was added to precipitate the yellow product. The crude product was filtered, washed with several portions of hexane, and air-dried. The material thus obtained was reprecipitated three times from THF solution using hexane. Recrystallization from methanol afforded 5.6 g (77%) of 2-[p-carbophenoxyphenyl]-5,6-bis(p-toluenesulfonamido)-benzimidazole as an amorphous yellow powder.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux under nitrogen (frothing)
  3. temperaturewas maintained at that temperature for 2 hours
  4. distillationThe solution was then distilled to half of the original volume, and heptane
  5. additionwas added
  6. customto precipitate the yellow product
  7. filtrationThe crude product was filtered
  8. washwashed with several portions of hexane
  9. customair-dried
  10. customThe material thus obtained
  11. customwas reprecipitated three times from THF solution
  12. customRecrystallization from methanol

Sources & evidence

ORD record
ord-94f9320b3d8f4d16a51187b5530f91fc
Source dataset
uspto-grants-1977_01
Patent number
US04001268

Reaction notes

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