Ammonium Hydroxide → HCID 86760365, compound

HRID 1375054Notes

Reaction equation

HRID 1375054 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:13]=[C:12]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)[S:11][C:10]=1[C:21]([OH:23])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N1C=CN=C1)([N:26]1C=CN=C1)=O.[OH-].[NH4+]>CN(C=O)C.[Cl-].[Na+].O>[C:1]([O:5][C:6](=[O:7])[NH:8][C:9]1[CH:13]=[C:12]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)[S:11][C:10]=1[C:21](=[O:23])[NH2:26])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 14923Ammonium HydroxideHCID 682631,1'-CarbonyldiimidazoleHCID 2757211HCID 2757211, compound

Product 1

HCID 86760365HCID 86760365, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of 1b (1.3 g, 3.7 mmol) in DMF (10 mL) was added 1,1′-carbonyl diimidazole (1.2 g, 7.4 mmol). The resultant solution was stirred for 1 h and mixed with ammonium hydroxide (37%, 5 mL). The mixture was diluted with brine solution (100 mL) and extracted with ethyl acetate (100 mL). The combined organic phases were dried over MgSO4, filtered, and concentrated. Flash chromatography (hexanes/ethyl acetate, 4:1) then provided compound 1c as a yellow solid.

Workup

  1. extractionextracted with ethyl acetate (100 mL)
  2. dry with materialThe combined organic phases were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-17976bdbb2ac4e418b7e3f3708c55f08
Source dataset
uspto-grants-2007_01
Patent number
US07166639B2

Reaction notes

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