Dichloromethane → HCID 178512708, compound

HRID 2309110Notes

Reaction equation

HRID 2309110 reaction equation
Cl.Cl.Cl.[NH:4]([C:8]1[S:9][CH:10]=[C:11]([CH2:13][S:14][CH2:15][CH2:16][NH:17][C:18](=[NH:22])[C:19](=[NH:21])[NH2:20])[N:12]=1)[C:5]([NH2:7])=[NH:6].C(Cl)Cl.[S:26](N1C(=O)C2=CC=CC=C2C1=O)N1C(=O)C2=CC=CC=C2C1=O.[OH-].[Na+]>C(N(CC)CC)C>[NH2:21][C:19]1[C:18]([NH:17][CH2:16][CH2:15][S:14][CH2:13][C:11]2[N:12]=[C:8]([NH:4][C:5]([NH2:7])=[NH:6])[S:9][CH:10]=2)=[N:22][S:26][N:20]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 821962,2'-Thiobis(1H-isoindole-1,3(2H)-dione)HCID 178478604HCID 178478604, compound

Product 1

HCID 178512708HCID 178512708, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A mixture of crude N-{2-[(2-guanidinothiazol-4-yl)methylthio]ethyl}ethanediimidamide trihydrochloride (5.65 g, 13.7 mmoles) [prepared in Step A], 50 ml of CH2Cl2 and 5.7 ml of triethylamine was treated with N,N'-thiobisphthalimide (DMF solvate) (5.44 g; 13.7 mmoles) and stirred for one hour to give a thick suspension. The mixture was treated with 40 ml of 2N NaOH and the solvents were decanted from the gum-like material which had separated. The gum was washed with 40 ml of 2N NaOH, water, and then dissolved in methanol and concentrated to give 3.0 g of crude product. The product was purified by flash chromatography on 90 g of silica gel (230-400 mesh) using ethyl acetate-methanol (97:3) as the eluent to give 2.44 g (54%) of the title compound. Treatment of the product in 35 ml of acetone with one equivalent of cyclohexylsulfamic acid gave the salt which was then recrystallized from 95% aqueous ethanol to give the title compound as its cyclohexylsulfamate salt, mp. 171°-173.5° C.

Workup

  1. customto give a thick suspension
  2. customthe solvents were decanted from the gum-like material which
  3. customhad separated
  4. washThe gum was washed with 40 ml of 2N NaOH, water
  5. dissolutiondissolved in methanol
  6. concentrationconcentrated
  7. customto give 3.0 g of crude product
  8. customThe product was purified by flash chromatography on 90 g of silica gel (230-400 mesh)

Sources & evidence

ORD record
ord-82f758344bc842a19a974eb6f3f6e93c
Source dataset
uspto-grants-1987_09
Patent number
US04692531

Reaction notes

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