Dichloromethane → HCID 21507562, compound

HRID 1287263Notes

Reaction equation

HRID 1287263 reaction equation
[NH2:1][CH:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([S:11]([N:14](C)[C:15]([NH:17][CH:18]3[CH2:22][CH2:21][CH2:20][CH2:19]3)=[O:16])(=[O:13])=[O:12])[CH:8]=2)[CH2:3]1.[OH-].[Na+].[Cl:26][C:27]1[CH:28]=[CH:29][C:30]([O:36][CH3:37])=[C:31]([CH:35]=1)[C:32](Cl)=[O:33].[CH2:38](Cl)Cl>O>[Cl:26][C:27]1[CH:28]=[CH:29][C:30]([O:36][CH3:37])=[C:31]([CH:35]=1)[C:32]([NH:1][CH:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([S:11]([NH:14][C:15]([NH:17][CH2:18][CH:22]3[CH2:21][CH2:20][CH2:19][CH2:38]3)=[O:16])(=[O:12])=[O:13])[CH:8]=2)[CH2:3]1)=[O:33]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 123841765-Chloro-2-methoxybenzoyl chlorideHCID 21507557HCID 21507557, compound

Product 1

HCID 21507562HCID 21507562, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2.4 g of N-(2-aminoindane-5-sulfonyl)-N'-cyclopentyl-methylurea (melting point 192° - 194° C, prepared by saponification of 2-N-(acetamido-indane-5-sulfonyl)-N'-cyclopentyl-methyl-urea, melting point 107° - 109° C) were dissolved in 10 ml of water and 3.6 ml of 2N-sodium hydroxide solution. Then, a solution of 1.7 g of 5-chloro-2-methoxy-benzoyl chloride in 6 ml of methylene chloride was added dropwise, while cooling, and the whole was stirred for 1 hour; the mixture was slowly heated and the methylene chloride was evaporated. The sulfonyl-urea that had precipitated was filtered off with suction and dissolved in dilute sodium hydroxide solution. The whole was then treated with active charcoal, filtered and the sodium salt was precipitated by the addition of concentrated sodium hydroxide solution. The sodium salt was dissolved in water and precipitated again by the addition of sodium hydroxide solution. Finally, the free compound was precipitated from the alkaline solution with hydrochloric acid and recrystallized from methanol. Melting point 194° - 196° C.

Workup

  1. temperaturewhile cooling
  2. temperaturethe mixture was slowly heated
  3. customthe methylene chloride was evaporated
  4. customThe sulfonyl-urea that had precipitated
  5. filtrationwas filtered off with suction
  6. dissolutiondissolved in dilute sodium hydroxide solution
  7. additionThe whole was then treated with active charcoal
  8. filtrationfiltered
  9. customthe sodium salt was precipitated by the addition of concentrated sodium hydroxide solution
  10. dissolutionThe sodium salt was dissolved in water
  11. customprecipitated again by the addition of sodium hydroxide solution
  12. customFinally, the free compound was precipitated from the alkaline solution with hydrochloric acid
  13. customrecrystallized from methanol

Sources & evidence

ORD record
ord-3ceb25fe53544daa89a96d83852c7772
Source dataset
uspto-grants-1976_10
Patent number
US03984416

Reaction notes

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