Hydrochloric Acid → HCID 22161736, compound

HRID 1088700Notes

Reaction equation

HRID 1088700 reaction equation
[H-].[Na+].[CH3:3][S:4]([NH:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[CH2:14][N:13]([C:18](=O)[CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH2:12][CH2:11]2)(=[O:6])=[O:5].[CH3:28]I.[ClH:30]>CN(C)C=O>[ClH:30].[CH3:28][N:7]([C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[CH2:14][N:13]([CH2:18][CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH2:12][CH2:11]2)[S:4]([CH3:3])(=[O:6])=[O:5]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 15718721HCID 15718721, compound

Product 1

HCID 22161736HCID 22161736, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of sodium hydride (0.17 g) in dimethylformamide (10 mL) at 0 C is added a solution of Example 22 (1.0 g) in dry dimethylformamide (10 mL). After stirring for 30 minutes, the reaction is treated with methyl iodide (0.5 mL), warmed to room temperature and allowed to stir for 12 hours. The reaction mixture is poured into cold 10% HCl and the product extracted out with CH2Cl2. The organic phases are combined, washed with brine, dried over MgSO4, filtered and concentrated. Using the procedure outlined in Example 2, the resulting residue can be reduced to provide after chromatography on silica gel and salt formation the desired product.

Workup

  1. stirringto stir for 12 hours
  2. extractionthe product extracted out with CH2Cl2
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-e151fab2f4a74069bb35eb5413a3c799
Source dataset
uspto-grants-1990_10
Patent number
US04963563

Reaction notes

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