Hydrochloric Acid → 3-Amino-4-[3-(3-pyrrolidinomethylphenoxy)propylamino]-1,2,5-thiadiazole

HRID 1982227Notes

Reaction equation

HRID 1982227 reaction equation
Cl.Cl.Cl.[N:4]1([CH2:9][C:10]2[CH:11]=[C:12]([CH:23]=[CH:24][CH:25]=2)[O:13][CH2:14][CH2:15][CH2:16][NH:17][C:18](=[NH:22])[C:19](=[NH:21])[NH2:20])[CH2:8][CH2:7][CH2:6][CH2:5]1.C(Cl)Cl.[S:29](N1C(=O)C2=CC=CC=C2C1=O)N1C(=O)C2=CC=CC=C2C1=O.Cl>C(O)CC.C(N(CC)CC)C>[NH2:21][C:19]1[C:18]([NH:17][CH2:16][CH2:15][CH2:14][O:13][C:12]2[CH:23]=[CH:24][CH:25]=[C:10]([CH2:9][N:4]3[CH2:8][CH2:7][CH2:6][CH2:5]3)[CH:11]=2)=[N:22][S:29][N:20]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 821962,2'-Thiobis(1H-isoindole-1,3(2H)-dione)HCID 178478599HCID 178478599, compound

Product 1

HCID 133136933-Amino-4-[3-(3-pyrrolidinomethylphenoxy)propylamino]-1,2,5-thiadiazole

Reagents, catalysts & solvents 2

HCID 10311-PropanolSolventHCID 8471TriethylamineSolvent

Procedure

A mixture of N-[3-(3-pyrrolidinomethylphenoxy)propyl]ethanediimidamide trihydrochloride (22.0 g; 53.0 mmoles) [prepared in Example 4, Step A],200 ml of CH2Cl2 and 22 ml of triethylamine was treated with N,N'-thiobisphthalimide (DMF solvate) (21.2 g; 53.0 mmoles). After stirring at ambient temperature for one hour, the mixture was washed with 100 ml of 20% KOH, dried (MgSO4), filtered, diluted with 100 ml of toluene and concentrated. The product was treated with one equivalent of aqueous HCl in 1-propanol to give 13.2 g (67%) of the hydrochloride salt of the title compound, mp 135°-137° C.

Workup

  1. washthe mixture was washed with 100 ml of 20% KOH
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. additiondiluted with 100 ml of toluene
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-226830cd87a9423884678bb005136f17
Source dataset
uspto-grants-1986_06
Patent number
US04595758

Reaction notes

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