Ethanol → HCID 18599045, compound

HRID 485677Notes

Reaction equation

HRID 485677 reaction equation
C(O)C.NC(N)=S.Br.Br.[NH2:10][C:11]1[S:12][C:13]2[CH2:22][C@H:21]3[C@@H:16]([CH2:17][CH2:18][CH2:19][N:20]3[CH3:23])[CH2:15][C:14]=2[N:24]=1.[OH-].[NH4+]>C(Cl)(Cl)Cl.CO>[NH2:10][C:11]1[S:12][C:13]2[CH2:22][C@H:21]3[C@@H:16]([CH2:17][CH2:18][CH2:19][N:20]3[CH3:23])[CH2:15][C:14]=2[N:24]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 14923Ammonium HydroxideHCID 2723790ThioureaHCID 131714313HCID 131714313, compound

Product 1

HCID 18599045HCID 18599045, compound

Reagents, catalysts & solvents 1

HCID 21584188Chloroform methanolSolvent

Procedure

About 10.8 millimole of the above hydrobromide salt were dissolved in 30 ml. of anhydrous ethanol to which had been added 1.03 g. of thiourea. The reaction was carried out and the product isolated according to the procedure of Example 1. Trans-(±)-2-amino-5-methyl-4,4a,5,6,7,8,8a,9-octahydrothiazolo[4,5-g]quinoline, dihydrobromide salt thus prepared was twice crystallized from methanol to yield 0.61 g. of a colorless crystalline solid melting above 235° C. TLC using 4:1 chloroform-methanol with a trace of aqueous ammonium hydroxide as the solvent system gave a single spot; Rf =0.30.

Workup

  1. customthe product isolated
  2. customwas twice crystallized from methanol
  3. customto yield 0.61 g
  4. custommelting above 235° C
  5. customgave a single spot

Sources & evidence

ORD record
ord-55943e36592c4869a799c4a9c8e4ccc8
Source dataset
uspto-grants-1985_08
Patent number
US04537893

Reaction notes

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