HCID 86681241, compound → HCID 86681240, compound

HRID 1848267Notes

Reaction equation

HRID 1848267 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH2:11][C:12]2[CH:22]=[CH:21][C:15]3[N:16]=[C:17]([S:19][CH3:20])[S:18][C:14]=3[CH:13]=2)[CH:9]=O)=[C:4]([N+:23]([O-])=O)[CH:3]=1>CCO.CC(O)=O.[Fe]>[I:1][C:2]1[CH:7]=[CH:6][C:5]2[N:8]([CH2:11][C:12]3[CH:22]=[CH:21][C:15]4[N:16]=[C:17]([S:19][CH3:20])[S:18][C:14]=4[CH:13]=3)[CH:9]=[N:23][C:4]=2[CH:3]=1

Participants

5

Reactant 1

HCID 86681241HCID 86681241, compound

Product 1

HCID 86681240HCID 86681240, compoundYield 68%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

A stirred mixture of N-(4-iodo-2-nitrophenyl)-N-((2-(methylthio)benzo[d]thiazol-6-yl)methyl)formamide and iron powder (16.7 g, 20 mmol) in EtOH (140 mL) and HOAc (60 mL) was heated at reflux for 1 h. The mixture was cooled to rt and filtered, and the filtrate was concentrated under reduced pressure. The residue was partitioned between EtOAc (200 mL) and 0.5 M aq Na2CO3 (100 mL). The organic layer was separated and further washed with brine (100 mL), dried over MgSO4, filtered, and concentrated under reduced pressure to afford 6-((5-iodo-1H-benzo[d]imidazol-1-yl)methyl)-2-(methylthio)benzo[d]thiazole (5.9 g, 68%) as a yellow solid that did not require further purification. 1H NMR (500 MHz, DMSO-d6) δ 8.44 (s, 1H), 8.03 (d, J=1.0 Hz, 1H), 7.97 (s, 1H), 7.80 (d, J=8.4 Hz, 1H), 7.49 (dd, J=1.4, 8.5 Hz, 1H), 7.37-7.43 (m, 2H), 5.60 (s, 2H), 2.76 (s, 3H); LCMS (ESI) m/z 438 (M+H)+.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1 h
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was partitioned between EtOAc (200 mL) and 0.5 M aq Na2CO3 (100 mL)
  6. customThe organic layer was separated
  7. washfurther washed with brine (100 mL)
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-55344fbb390f46dab306092e3810abc2
Source dataset
uspto-grants-2015_02
Patent number
US08952058B2

Reaction notes

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