Ammonia → Cyclopentylurea

HRID 1580465Notes

Reaction equation

HRID 1580465 reaction equation
[Na].C1(S(N)(=O)=O)C=CC=CC=1.[CH:12]1([NH:17][C:18]([NH:20]C2CCCC2)=[O:19])[CH2:16][CH2:15][CH2:14][CH2:13]1.N>>[CH:12]1([NH:17][C:18](=[O:19])[NH2:20])[CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

5

Reactant 4

HCID 222AmmoniaHCID 7370BenzenesulfonamideHCID 5360545SodiumHCID 13812604N,N'-Dicyclopentylurea

Product 1

HCID 294526Cyclopentylurea

Conditions

Temperature
220 °C

Procedure

2 g of sodium salt of 4-(β-<2-methoxy-5-chlorobenzamido>-ethyl)-benzenesulfonamide and 2.2 g of N,N'-dicyclopentyl-urea (m.p. 248° - 249°C, prepared from cyclopentyl-isocyanate and cyclopentyl-amine) were well mixed in a mortar. The mixture was heated to 220°C for 10 minutes in an Erlenmeyer flask on a pre-heated oil bath. After cooling, the sintered reaction cake was treated with 0.5 %-ammonia. After filtration, the filtrate was acidified and a precipitate was obtained which was separated by suction-filtration and dissolved once more in 0.5 %-ammonia. After filtration, the filtrate was acidified. The precipitate of crude N-[4-(β-<2-methoxy-5-chlorobenzamide>-ethyl)-benzenesulfonyl]-N'-cyclopentyl-urea that had separated was isolated by suction-filtration and dried. By treatment with methanol an at first smeary and then crystalline substance was obtained, which after suction-filtration, was once more recrystallized from methanol. The melting point of N-[4-(β-<2-methoxy-5-chloro-benzamido>-ethyl)-benzenesulfonyl]-N'-cyclopentyl-urea obtained was 182° - 184°C.

Workup

  1. temperatureAfter cooling
  2. filtrationAfter filtration
  3. customa precipitate was obtained which
  4. customwas separated by suction-filtration
  5. dissolutiondissolved once more in 0.5 %-ammonia
  6. filtrationAfter filtration
  7. customThe precipitate of crude N-[4-(β-<2-methoxy-5-chlorobenzamide>-ethyl)-benzenesulfonyl]-N'-cyclopentyl-urea that had separated
  8. customwas isolated by suction-filtration
  9. customdried
  10. customBy treatment with methanol an at first smeary and then crystalline substance was obtained
  11. filtrationwhich after suction-filtration
  12. customwas once more recrystallized from methanol

Sources & evidence

ORD record
ord-3f64cabaee224f418f86ee5de928dc91
Source dataset
uspto-grants-1976_01
Patent number
US03932658

Reaction notes

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