Hydrochloric Acid → HCID 23085781, compound

HRID 2243086Notes

Reaction equation

HRID 2243086 reaction equation
O.Cl.[CH3:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[S:12][C:13]3[CH:19]=[CH:18][C:17]([N+:20]([O-])=O)=[CH:16][C:14]=3[N:15]=2)=[CH:7][CH:6]=1>C(O)C.[Fe]>[CH3:3][O:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]2[S:12][C:13]3[CH:19]=[CH:18][C:17]([NH2:20])=[CH:16][C:14]=3[N:15]=2)=[CH:9][CH:10]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 23085607HCID 23085607, compound

Product 1

HCID 23085781HCID 23085781, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

Iron powder (45.9 g, 0.822 mol), water (70 ml) and 37% hydrochloric acid (1.6 ml, 0.019 mol) are added to 2-(4-methoxyphenyl)-5-nitrobenzothiazole (10.95 g, 0.038 mol) in ethanol (300 ml). The mixture is heated at 80° C. for one hour. The resulting mixture is filtered and evaporated, and the residue is taken up in ethyl acetate and basified with NaOH (pH=11). The organic phase is filtered and washed with water. The resulting solution is evaporated and the product obtained is recrystallized from isopropyl ether. Yield: (61%); Rf (9/1 chloroform/methanol): 0.60; Elem. anal. C14H12N2OS; theory C, 65.60; H, 4.72; N, 10.93. found C, 65.44; H, 4.87; N, 10.37. IR (KBr): 3440, 3320, 1600, 1465, 1245, 1170 cm−1.

Workup

  1. filtrationThe resulting mixture is filtered
  2. customevaporated
  3. filtrationThe organic phase is filtered
  4. washwashed with water
  5. customThe resulting solution is evaporated
  6. customthe product obtained
  7. customis recrystallized from isopropyl ether

Sources & evidence

ORD record
ord-12902efd82ac47be92211809a0718171
Source dataset
uspto-grants-2010_03
Patent number
US07674809B2

Reaction notes

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