Sodium Pyrosulfite → HCID 178513574, compound

HRID 2247151Notes

Reaction equation

HRID 2247151 reaction equation
[C:1]1([C:7]2([C:12]3[CH:17]=[CH:16][C:15]([C:18]4[NH:22][C:21]5[CH:23]=[CH:24][C:25]([C:27]([NH2:29])=[O:28])=[CH:26][C:20]=5[N:19]=4)=[CH:14][CH:13]=3)[O:11][CH2:10][CH2:9][O:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.NC1C=C(C=CC=1N)C(N)=O.C1(C2(C3C=CC(C=O)=CC=3)OCCO2)C=CC=CC=1.S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+]>CN(C=O)C>[NH3:19].[C:1]1([C:7]2([C:12]3[CH:17]=[CH:16][C:15]([C:18]4[NH:22][C:21]5[CH:23]=[CH:24][C:25]([C:27]([NH2:29])=[O:28])=[CH:26][C:20]=5[N:19]=4)=[CH:14][CH:13]=3)[O:8][CH2:9][CH2:10][O:11]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 656671Sodium PyrosulfiteHCID 10706104HCID 10706104, compoundHCID 212178433,4-DiaminobenzamideHCID 178513574HCID 178513574, compound

Product 2

HCID 222AmmoniaYield 9%HCID 178513574HCID 178513574, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

2-[4-(2-Phenyl-[1,3]dioxolan-2-yl)-phenyl]-1H-benzoimidazole-5-carboxylic acid amide. To a solution of 3,4-diamino-benzamide (100 mg, 0.6 mmol) in anhydrous DMF was added 4-(2-phenyl-[1,3]dioxolan-2-yl)-benzaldehyde (168 mg, 0.6 mmol) and sodium metabisulfite (164 mg, 0.86 mmol). The mixture was heated to 90° C. under N2 for 16 h. The reaction mixture was cooled and added dropwise to ice/H2O. The resulting solids were filtered and washed with H2O (59 mL) then hexanes (2×50 mL). Purification by chromatography; (silica gel, 1% 1 methanol saturated with ammonia/9% methanol/CH2Cl2) afforded 160 mg (63%) of the title compound. TLC (silica, 1% methanol-saturated with ammonia/9% methanol/CH2Cl2): Rf=0.3. HPLC (Method A): Rt=7.02. MS (ESI+): mass calculated for C23H19N3O3, 385.1; m/z found, 386.1 [M+H]+. 1H NMR (400 MHz, CD3OD): δ 8.13 (br s, 1H), 8.04 (d, J=8.4 Hz, 2H), 7.77 (d, J=8.5 Hz, 1H), 7.64 (d, J=8.4 Hz, 2H), 7.58 (br s, 1H), 7.49-7.47 (dd, J=8.4. 1.5 Hz, 2H), 7.32-7.23 (m, 3H), 4.03 (s, 4H).

Workup

  1. temperatureThe reaction mixture was cooled
  2. filtrationThe resulting solids were filtered
  3. washwashed with H2O (59 mL)
  4. customPurification by chromatography

Sources & evidence

ORD record
ord-6eb2681116974fbd9b57d751e589a1b5
Source dataset
uspto-grants-2010_03
Patent number
US07687639B2

Reaction notes

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