Hydrochloric Acid → 1-cyclohexyl-3-[(3-dimethylcarbamoyl-2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl)sulfonyl]urea

HRID 2398159Notes

Reaction equation

HRID 2398159 reaction equation
[OH-].[Na+].[CH3:3][N:4]([CH3:22])[C:5]([N:7]1[CH2:13][CH2:12][C:11]2[CH:14]=[CH:15][C:16]([S:18]([NH2:21])(=[O:20])=[O:19])=[CH:17][C:10]=2[CH2:9][CH2:8]1)=[O:6].[CH:23]1([N:29]=[C:30]=[O:31])[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1.Cl>O.CC(C)=O>[CH:23]1([NH:29][C:30]([NH:21][S:18]([C:16]2[CH:15]=[CH:14][C:11]3[CH2:12][CH2:13][N:7]([C:5](=[O:6])[N:4]([CH3:22])[CH3:3])[CH2:8][CH2:9][C:10]=3[CH:17]=2)(=[O:20])=[O:19])=[O:31])[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 18502Cyclohexyl isocyanateHCID 21434451HCID 21434451, compound

Product 1

HCID 214344341-cyclohexyl-3-[(3-dimethylcarbamoyl-2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl)sulfonyl]urea

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

8.8 Ml. of 2N sodium hydroxide are added while stirring at 25° C. to a mixture of 5.2 g. of 3-dimethylcarbamoyl-2,3,4,5-tetrahydro-1H-3-benzazepine-7-sulfonamide in 180 ml. of acetone, during which the solid material first dissolves and then a new crystalline precipitate immediately results. 2.26 Ml. of cyclohexylisocyanate are then added thereto while cooling externally with ice and stirring, whereupon the solid material passes completely into solution and then a crystalline precipitate soon reappears. The mixture is subsequently stirred for 16 hours at 25° C., then diluted with 350 ml. of water, acidified to pH 2 with 3N hydrochloric acid and finally extracted twice with 500 ml. of chloroform each time. The chloroform extracts are dried over sodium sulfate and evaporated in vacuo at 60° C. The residue is dissolved in 25 ml. of acetone and crystallized by trituration. There is obtained 1-cyclohexyl-3-[(3-dimethylcarbamoyl-2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl)sulfonyl]urea, m.p. 113° C. (with decomposition).

Workup

  1. customa new crystalline precipitate immediately results
  2. temperaturewhile cooling externally with ice
  3. stirringstirring, whereupon the solid material passes completely into solution
  4. stirringThe mixture is subsequently stirred for 16 hours at 25° C.
  5. additiondiluted with 350 ml
  6. extractionfinally extracted twice with 500 ml
  7. dry with materialThe chloroform extracts are dried over sodium sulfate
  8. customevaporated in vacuo at 60° C
  9. dissolutionThe residue is dissolved in 25 ml
  10. customof acetone and crystallized by trituration

Sources & evidence

ORD record
ord-710d7c87fe6641f0bcb3175db5ad0fa3
Source dataset
uspto-grants-1977_05
Patent number
US04024128

Reaction notes

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