Water → HCID 20544691, compound

HRID 1660013Notes

Reaction equation

HRID 1660013 reaction equation
O1CCOCC1.O.[C:8]12([NH:18][S:19]([C:22]3[CH:23]=[C:24]([C:32](O)=[O:33])[C:25]4[O:30][CH2:29][CH2:28][O:27][C:26]=4[CH:31]=3)(=[O:21])=[O:20])[CH2:17][CH:12]3[CH2:13][CH:14]([CH2:16][CH:10]([CH2:11]3)[CH2:9]1)[CH2:15]2.[CH2:35]([NH2:39])[CH2:36][CH2:37][CH3:38]>C(N(CC)CC)C>[CH2:35]([NH:39][C:32]([C:24]1[C:25]2[O:30][CH2:29][CH2:28][O:27][C:26]=2[CH:31]=[C:22]([S:19](=[O:21])(=[O:20])[NH:18][C:8]23[CH2:15][CH:14]4[CH2:13][CH:12]([CH2:11][CH:10]([CH2:16]4)[CH2:9]2)[CH2:17]3)[CH:23]=1)=[O:33])[CH2:36][CH2:37][CH3:38]

Participants

6

Reactant 4

HCID 962WaterHCID 8007ButylamineHCID 312751,4-DioxaneHCID 20544697HCID 20544697, compound

Product 1

HCID 20544691HCID 20544691, compoundYield 46.5%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

500 ml of dioxane, 50 ml of water, 49 g of 7-[(1-adamantyl)-sulfamoyl]-1,4-benzodioxane-5-carboxylic acid and 12.5 g of triethylamine were introduced into a 2-liter balloon flask provided with an agitator and a thermometer. The solution was agitated at ambient temperature and then 17 g of isobutyl chloroformiate was added. The mixture was agitated and then 10 g of butylamine was introduced. After agitation of the mixture dioxane was removed. The residue was dissolved in 200 ml of hot water. The crystals formed by cooling were washed with water, dried and redissolved in 250 ml of acetone at boiling temperature. The solution was filtered hot. The crystals formed by cooling were dried off, washed and dried. 26 g of N-(butyl)-7-[(1-adamantyl)sulfamoyl]-1,4-benzodioxane-5-carboxamide was produced (M.P. 147° C.; yield: 46.4%).

Workup

  1. customprovided with an agitator
  2. addition17 g of isobutyl chloroformiate was added
  3. stirringThe mixture was agitated
  4. customAfter agitation of the mixture dioxane was removed
  5. dissolutionThe residue was dissolved in 200 ml of hot water
  6. customThe crystals formed
  7. temperatureby cooling
  8. washwere washed with water
  9. customdried
  10. dissolutionredissolved in 250 ml of acetone
  11. filtrationThe solution was filtered hot
  12. customThe crystals formed
  13. temperatureby cooling
  14. customwere dried off
  15. washwashed
  16. customdried

Sources & evidence

ORD record
ord-cf63c060d09e447c9285b9de1d401176
Source dataset
uspto-grants-1981_12
Patent number
US04306072

Reaction notes

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