Hydrochloric Acid → HCID 13041824, compound

HRID 1156603Notes

Reaction equation

HRID 1156603 reaction equation
N[C:2]1[S:3][C:4]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][CH:8]=2)[N:6]=1.NC(N)=S.[ClH:25].N([O-])=O.[Na+]>Cl[Cu].O.CC(O)=O>[Cl:25][C:2]1[S:3][C:4]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][CH:8]=2)[N:6]=1

Participants

8

Reactant 4

HCID 313Hydrochloric Acid2×HCID 721634Ethyl 2-amino-4-(4-nitrophenyl)-1,3-thiazole-5-carboxylate2×HCID 2723790ThioureaHCID 23668193Sodium Nitrite

Product 1

HCID 13041824HCID 13041824, compound

Reagents, catalysts & solvents 3

HCID 62652Cuprous chlorideCatalystHCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

Ethyl 2-chloro-p-nitrobenzoylacetate, obtained from ethyl p-nitrobenzoylacetate and sulfuryl chloride in accordance with the procedure of Balog et al, Studio. Univ. Bebes. Boylai., Vol. 1, No. 2, Page 155 (1960), was converted to ethyl 2-amino-4-p-nitrophenyl-5-thiazolecarboxylate with thiourea in accordance with a procedure in the above-mentioned publication. To a cooled (15° C.) solution of 10.0 g (0.0334 mole) of ethyl 2-amino-4-(p-nitrophenyl)-5-thiazolecarboxylate in 100 ml. of concentrated HCl and 100 ml. of glacial HOAc was added 7.0 g (0.101 mole) of NaNO2 in 15 minutes. The reaction mixture was stirred for 10 minutes and poured into a solution of 3.78 g (0.038 mole) of CuCl in 60 ml. of concentrated HCl. A slow gas evolution occurred which was accelerated when 50 ml. of water was added to the reaction mixture. The reaction mixture gradually turned yellow with precipitation of white solid. The precipitate was extracted with CHCl3. The CHCl3 solution was dried (MgSO4) and concentrated under reduced pressure. The residue was boiled with hot MeOH and filtered. The solid was recrystallized from acetone-chloroform to give 2.4 g of the desired product, m.p. 146°-148° C.

Workup

  1. customThe reaction mixture gradually turned yellow with precipitation of white solid
  2. extractionThe precipitate was extracted with CHCl3
  3. dry with materialThe CHCl3 solution was dried (MgSO4)
  4. concentrationconcentrated under reduced pressure
  5. filtrationfiltered
  6. customThe solid was recrystallized from acetone-chloroform

Sources & evidence

ORD record
ord-9794e29830a34c65b07a17b3d39e5b05
Source dataset
uspto-grants-1982_06
Patent number
US04336389

Reaction notes

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