Sulfamic Acid → HCID 69282254, compound

HRID 1293489Notes

Reaction equation

HRID 1293489 reaction equation
[CH3:1][O:2][C:3]1[C:15]2[N:14]([CH3:16])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7]=2[C:6]([CH:17]=[O:18])=[CH:5][CH:4]=1.S(=O)(=O)([OH:21])N.Cl([O-])=O.[Na+]>CC(C)=O.O>[CH3:1][O:2][C:3]1[C:15]2[N:14]([CH3:16])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7]=2[C:6]([C:17]([OH:21])=[O:18])=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 5987Sulfamic AcidHCID 23668197Sodium ChloriteHCID 85967074HCID 85967074, compound

Product 1

HCID 69282254HCID 69282254, compoundYield 88.9%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent2×

Conditions

Temperature
25 °C

Procedure

To a solution of 1-methoxy-9-methyl 9H-4-carbazolecarbaldehyde (100 mg 0.4184 mmoles) in a mixture of 8 mL acetone and 4 mL water, sulfamic acid (48.7 mg 0.502 mmoles) was added followed by a solution of sodium chlorite (37.8 mg, 0.4184 mmoles) in 2 mL water and the reaction mixture was stirred at 25° C. for 4 hrs. Acetone from the reaction mixture was evaporated under reduced pressure, diluted with ethyl acetate 30 mL. Organic layer was separated and basified with freshly prepared sodium bicarbonate solution and separated the aqueous layer and acidified with 1N HCl and extracted with ethyl acetate (2×25 mL). Ethyl acetate layer was washed with brine (2×20 mL), dried over sodium sulfate and concerted to give 95 mg of the tide compound.

Workup

  1. additionwas added
  2. customAcetone from the reaction mixture was evaporated under reduced pressure
  3. additiondiluted with ethyl acetate 30 mL
  4. customOrganic layer was separated
  5. customseparated the aqueous layer
  6. extractionextracted with ethyl acetate (2×25 mL)
  7. washEthyl acetate layer was washed with brine (2×20 mL)
  8. dry with materialdried over sodium sulfate

Sources & evidence

ORD record
ord-573d15d5c04245278a588db72c4951b8
Source dataset
uspto-grants-2007_07
Patent number
US07238725B2

Reaction notes

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