Hydrochloric Acid → HCID 20393357, compound

HRID 1863076Notes

Reaction equation

HRID 1863076 reaction equation
[CH3:1][NH:2][C:3]([C:5]1[N:6]([CH3:21])[C:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[C:8]2[C:13]=1[CH:12]=[CH:11][C:10]([Cl:14])=[CH:9]2)=[O:4].[CH2:22]([N:24]([CH2:27][CH2:28]Cl)[CH2:25][CH3:26])[CH3:23].Cl.[CH:31]1([NH:37][S:38](=[O:41])(=[O:40])[OH:39])[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1>C(OCC)C.C(O)(C)C.C1(C)C=CC=CC=1.CN(C)C=O>[CH:31]1([NH:37][S:38]([OH:41])(=[O:40])=[O:39])[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36]1.[CH2:25]([N:24]([CH2:22][CH3:23])[CH2:27][CH2:28][N:2]([CH3:1])[C:3]([C:5]1[N:6]([CH3:21])[C:7]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)=[C:8]2[C:13]=1[CH:12]=[CH:11][C:10]([Cl:14])=[CH:9]2)=[O:4])[CH3:26]

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 7533CyclamateHCID 13364Diethylaminoethyl chlorideHCID 54545674HCID 54545674, compound

Product 1

HCID 20393357HCID 20393357, compound

Reagents, catalysts & solvents 4

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolventHCID 3776IsopropanolSolventHCID 6228DimethylformamideSolvent

Procedure

A suspension of 15.0 g. of 5-chloro-2-methyl-3-phenylisoindole-1-carboxylic acid methylamide in 190 ml. of dimethylformamide is treated under an atmosphere of argon with 8.25 g. of potassium tertiary butylate and the mixture is stirred in an ice-bath for 15 minutes. At 0°-5° C., there is then added a solution of 0.1 mol. of diethylaminoethyl chloride in 150 ml. of toluene (freshly prepared from the corresponding hydrochloride and dried over sodium sulfate), the mixture is stirred first at room temperature for 30 minutes and then at 100° C. for 30 minutes. After cooling, the toluene is removed by distillation under reduced pressure and the residual solution poured on to 600 ml. of ice-water. The separated thick oil is extracted with methylene chloride, and the extract washed with a saturated sodium chloride solution, dried over sodium sulfate and concentrated to dryness. The residue obtained is dissolved in 60 ml. of isopropanol and treated with 9.0 g. of N-cyclohexylsulfamic acid. 200 Ml. of diethyl ether are gradually added and the mixture is left to stand at room temperature for 1 hour. The almost colorless salt which crystallizes out is removed by filtration, washed with a small amount of diethyl ether and dried in a desiccator. Recrystallization from acetone yields 5-chloro-2-methyl-3-phenylisoindole-1-carboxylic acid [2-(diethylamino)ethyl]methylamide cyclohexanesulfamate having a melting point of 166°-168° C. (decomposition).

Workup

  1. additionA suspension of 15.0 g
  2. additionAt 0°-5° C., there is then added a solution of 0.1 mol
  3. dry with materialdried over sodium sulfate), the mixture
  4. waitat 100° C. for 30 minutes
  5. temperatureAfter cooling
  6. customthe toluene is removed by distillation under reduced pressure
  7. additionthe residual solution poured on to 600 ml
  8. extractionThe separated thick oil is extracted with methylene chloride
  9. washthe extract washed with a saturated sodium chloride solution
  10. dry with materialdried over sodium sulfate
  11. concentrationconcentrated to dryness
  12. customThe residue obtained
  13. dissolutionis dissolved in 60 ml
  14. waitthe mixture is left
  15. waitto stand at room temperature for 1 hour
  16. customThe almost colorless salt which crystallizes out
  17. customis removed by filtration
  18. washwashed with a small amount of diethyl ether
  19. customdried in a desiccator
  20. customRecrystallization from acetone

Sources & evidence

ORD record
ord-85b953a36d324a709294ddc0ef304e2e
Source dataset
uspto-grants-1979_09
Patent number
US04167632

Reaction notes

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