Sulfuric Acid → HCID 53895465, compound

HRID 2398173Notes

Reaction equation

HRID 2398173 reaction equation
[CH3:1][N:2]([CH3:20])[C:3]([N:5]1[CH2:11][CH2:10][C:9]2[CH:12]=[CH:13][C:14]([S:16]([NH2:19])(=[O:18])=[O:17])=[CH:15][C:8]=2[CH2:7][CH2:6]1)=[O:4].C(=O)([O-])[O-].[K+].[K+].[CH2:27]([O:29][C:30](Cl)=[O:31])[CH3:28].S(=O)(=O)(O)O>C(Cl)(Cl)Cl.O.CC(C)=O>[CH2:27]([O:29][C:30](=[O:31])[NH:19][S:16]([C:14]1[CH:13]=[CH:12][C:9]2[CH2:10][CH2:11][N:5]([C:3](=[O:4])[N:2]([CH3:20])[CH3:1])[CH2:6][CH2:7][C:8]=2[CH:15]=1)(=[O:18])=[O:17])[CH3:28]

Participants

8

Reactant 4

HCID 1118Sulfuric AcidHCID 10928Ethyl chloroformateHCID 11430Potassium CarbonateHCID 21434451HCID 21434451, compound

Product 1

HCID 53895465HCID 53895465, compound

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolventHCID 6212ChloroformSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of 7.5 g. of 3-dimethylcarbamoyl-2,3,4,5-tetrahydro-1H-3-benzazepine-7-sulfonamide, 13.9 g. of potassium carbonate, 9.6 ml. of chloroformic acid ethyl ester and 150 ml. of acetone is heated to reflux for 16 hours while stirring, then cooled to 25° C. and poured on to a mixture of 500 ml. of water and 1000 ml. of chloroform. The pH of the aqueous phase is then brought to 2.0 with 6N sulfuric acid while stirring. The chloroform phase is subsequently separated, dried over sodium sulfate and evaporated in vacuo. The evaporation residue is crystallized by the addition of ether. There is obtained [(3-dimethylcarbamoyl-2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl)sulfonyl]carbamic acid ethyl ester of melting point 140°-141° C.

Workup

  1. additionA mixture of 7.5 g
  2. temperatureto reflux for 16 hours
  3. additionpoured on to a mixture of 500 ml
  4. stirringwhile stirring
  5. customThe chloroform phase is subsequently separated
  6. dry with materialdried over sodium sulfate
  7. customevaporated in vacuo
  8. customThe evaporation residue is crystallized by the addition of ether

Sources & evidence

ORD record
ord-a0de23aa74774fa68938310f523fa051
Source dataset
uspto-grants-1977_05
Patent number
US04024128

Reaction notes

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