Stannous chloride dihydrate → HCID 66980764, compound

HRID 272668Notes

Reaction equation

HRID 272668 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:10]=2[C:11](OC)=[O:12])=[C:4]([N+:20]([O-])=O)[CH:3]=1.O.O.Cl[Sn]Cl>Cl.CO>[Br:1][C:2]1[CH:7]=[CH:6][C:5]2[NH:8][C:9]3[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:10]=3[C:11](=[O:12])[NH:20][C:4]=2[CH:3]=1

Participants

5

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 69218742HCID 69218742, compound

Product 1

HCID 66980764HCID 66980764, compoundYield 91.1%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

A mixture of Example 2A (6.0 g, 15.6 mmol) and SnCl2.2H2O (10.54 g, 46.8 mmol) in 37% HCl (200 mL) and methanol (300 mL) was heated to reflux for 20 hours, cooled to room temperature, and filtered. The filter cake was washed with 1:1H2O/methanol and dried in a vacuum oven at 65° C. to provide 4.6 g (91%) of the desired product. MS (DCI) m/e 324 (M+H)+, 341 (M+NH4)+; 1H NMR (300 MHz, DMSO-d6) δ 9.98 (s, 1H), 8.18 (s, 1H), 7.69 (d, J=8.5 Hz, 1H), 7.12-7.16 (m, 2H), 7.05 (d, J=2 Hz, 1H), 6.95 (dd, J=8.4, 2 Hz, 1H), 6.91 (d, J=9.1 Hz, 1H).

Workup

  1. temperatureto reflux for 20 hours
  2. filtrationfiltered
  3. washThe filter cake was washed with 1:1H2O/methanol
  4. customdried in a vacuum oven at 65° C.

Sources & evidence

ORD record
ord-fa22a8bb482243d48db0a787cd24995c
Source dataset
uspto-grants-2008_11
Patent number
US07456169B2

Reaction notes

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