HCID 86674216, compound → HCID 86674218, compound

HRID 1897400Notes

Reaction equation

HRID 1897400 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[N:6]1[C:10]2[CH:11]=[C:12]([N+:23]([O-])=O)[C:13]([N+:20]([O-])=O)=[C:14]([C:15]3[S:16][CH:17]=[CH:18][CH:19]=3)[C:9]=2[NH:8][S:7]1>[Fe].C(O)(=O)C>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[N:6]1[C:10]2[CH:11]=[C:12]([NH2:23])[C:13]([NH2:20])=[C:14]([C:15]3[S:16][CH:17]=[CH:18][CH:19]=3)[C:9]=2[NH:8][S:7]1

Participants

4

Reactant 1

HCID 86674216HCID 86674216, compound

Product 1

HCID 86674218HCID 86674218, compoundYield 96.1%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

The 1,4-di(2-thienyl)-5,6-dinitro-2,1,3-benzothiadiazole (502 mg, 1.29 mmol) synthesized above was added to acetic acid (40 mL) together with iron dust (878 mg, 15.72 mmol) and reacted at 90° C. for 24 hours. The resulting solution was poured to distilled water and extracted with ether. The organic solvent layer was dried to obtain 1,4-di(2-thienyl)-5,6-diamino-2,1,3-benzothiadiazole (410 mg, 1.24 mmol, yield: 96%) as yellowish brown solid. 1H NMR (400 MHz, CDCl3, ppm): δ 7.56 (dd, 2H, J=5.5 Hz, J=1.1 Hz), 7.38 (dd, 2H, J=3.3 Hz, J=1.1 Hz), 7.26 (t, 2H, J=4.7 Hz), 4.38 (br, 4H).

Workup

  1. customreacted at 90° C. for 24 hours
  2. additionThe resulting solution was poured
  3. distillationto distilled water
  4. extractionextracted with ether
  5. customThe organic solvent layer was dried

Sources & evidence

ORD record
ord-5fd075afcf16414ea1efa90988c08f58
Source dataset
uspto-grants-2013_08
Patent number
US08519087B2

Reaction notes

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