Sulfamic Acid → HCID 86592863, compound

HRID 457397Notes

Reaction equation

HRID 457397 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][N:11]([C:22]3[N:26]([CH2:27][CH2:28][CH2:29][CH3:30])[C:25]([C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)=[N:24][C:23]=3[CH:37]=[O:38])[CH2:12][C:13]3[CH:21]=[CH:20][C:16]4[O:17][CH2:18][O:19][C:15]=4[CH:14]=3)=[CH:9][C:4]=2[O:3][CH2:2]1.S(=O)(=O)([OH:41])N.Cl([O-])=O.[Na+]>O>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][N:11]([C:22]3[N:26]([CH2:27][CH2:28][CH2:29][CH3:30])[C:25]([C:31]4[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=4)=[N:24][C:23]=3[C:37]([OH:41])=[O:38])[CH2:12][C:13]3[CH:21]=[CH:20][C:16]4[O:17][CH2:18][O:19][C:15]=4[CH:14]=3)=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

5

Reactant 3

HCID 5987Sulfamic AcidHCID 23668197Sodium ChloriteHCID 86592864HCID 86592864, compound

Product 1

HCID 86592863HCID 86592863, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 5-[(bis-benzo[1,3]dioxol-5-ylmethyl-amino]-1-butyl-2-phenyl-1H-imidazol-4-carbaldehyde 213 (263 mg, 0.5 mmol) in actone (10 mL) and water (5 mL) is added sulfamic acid (107 mg, 1.11 mmol) at room temperature and the mixture is stirred for 30 min. Sodium chlorite (63 mg, 0.7 mmol) is added and the mixture is stirred for additional 30 min at room temperature. Evaporation of most actone and the residue is extracted with chloroform. The organic phase is washed with water, brine and dried over sodium sulfate. The solvent is removed and the product is dried in vacuo. Yield: 281 mg; LC-MS (MH+): 542.

Workup

  1. stirringthe mixture is stirred for additional 30 min at room temperature
  2. customEvaporation of most actone
  3. extractionthe residue is extracted with chloroform
  4. washThe organic phase is washed with water, brine
  5. dry with materialdried over sodium sulfate
  6. customThe solvent is removed
  7. customthe product is dried in vacuo

Sources & evidence

ORD record
ord-1fc9d5d456034a7eb3d18771c1d32475
Source dataset
uspto-grants-2007_03
Patent number
US07186734B2

Reaction notes

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