Acetic Acid → HCID 21412118, compound

HRID 1284247Notes

Reaction equation

HRID 1284247 reaction equation
[CH3:1][N:2]([CH3:27])[S:3]([C:6]1[CH:7]=[CH:8][C:9]2[CH:15]=[CH:14][C:13]3[CH:16]=[CH:17][CH:18]=[CH:19][C:12]=3[CH:11]([CH2:20][CH2:21][CH2:22][N:23](C)[CH3:24])[C:10]=2[CH:26]=1)(=[O:5])=[O:4].N#CN.C(O)(=O)C.Cl>O>[CH3:27][N:2]([CH3:1])[S:3]([C:6]1[CH:7]=[CH:8][C:9]2[CH:15]=[CH:14][C:13]3[CH:16]=[CH:17][CH:18]=[CH:19][C:12]=3[CH:11]([CH2:20][CH2:21][CH2:22][NH:23][CH3:24])[C:10]=2[CH:26]=1)(=[O:4])=[O:5]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 9864Cyanamide2×HCID 21412135HCID 21412135, compound

Product 1

HCID 21412118HCID 21412118, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3-Dimethylsulfamoyl-5-(3-dimethylaminopropyl)-5H-dibenzo[a,d]cycloheptene is converted to the corresponding cyanamide by following the procedure of Example 17, Step B. The cyanamide (0.28 g., 0.00071 mole) together with 2.8 ml. of glacial acetic acid, 2.0 ml. of water and 0.4 ml. of concentrated hydrochloric acid is heated to refluxing for 29 hours. The reaction mixture is evaporated to dryness under reduced pressure and the residue is dissolved in water. The aqueous solution is made alkaline with sodium hydroxide and the oily base that separates is extracted into ether. The washed and dried ether extract is evaporated under reduced pressure, leaving 3-dimethylsulfamoyl-5-(3-methylaminopropyl)-5H-dibenzo[a,d]cycloheptene as an oil weighing 170 mg. The base may be converted to the hydrogen oxalate salt by dissolution in absolute ethanol, addition of an equimolar quantity of oxalic acid dissolved in ethanol, and precipitation by the addition of ether. After repeated recrystallizations from absolute ethanol and from isopropyl alcohol, the hydrogen oxalate melts at 133.5°-135.5°C., dec.

Workup

  1. temperatureto refluxing for 29 hours
  2. customThe reaction mixture is evaporated to dryness under reduced pressure
  3. dissolutionthe residue is dissolved in water
  4. extractionthe oily base that separates is extracted into ether
  5. washThe washed
  6. extractiondried ether extract
  7. customis evaporated under reduced pressure

Sources & evidence

ORD record
ord-189396efd28f4565ace3b128e0c0ae3a
Source dataset
uspto-grants-1976_08
Patent number
US03978121

Reaction notes

Loading…