Sulfamic Acid → HCID 66592347, compound

HRID 1091841Notes

Reaction equation

HRID 1091841 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][C:9]2[O:12][C:13]3[C:18]([O:19][CH3:20])=[CH:17][CH:16]=[C:15]([CH:21]=[O:22])[C:14]=3[C:8]=2[CH2:7]1)=[O:5])[CH3:2].S(=O)(=O)([OH:25])N.Cl([O-])=O.[Na+]>CC(C)=O.O>[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][C:9]2[O:12][C:13]3[C:18]([O:19][CH3:20])=[CH:17][CH:16]=[C:15]([C:21]([OH:25])=[O:22])[C:14]=3[C:8]=2[CH2:7]1)=[O:5])[CH3:2]

Participants

6

Reactant 3

HCID 5987Sulfamic AcidHCID 23668197Sodium ChloriteHCID 86636831HCID 86636831, compound

Product 1

HCID 66592347HCID 66592347, compoundYield 67.2%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

2-ethoxycarbonyl-6-methoxy-1,2,3,4-tetrahydro[1]benzofuro[3,2-c]pyridine-9-carbaldehyde (from step 8) (170 mg, 0.559 mmol) was dissolved in acetone (10 ml): water (2.5 ml). To this solution sulfamic acid (81.0 mg, 0.838 mmol) was added and then reaction was cooled to 0° C. Then sodium chlorite (85 mg, 0.950 mmol) in water (2.5 ml) was added drop wise to maintain temperature below 10° C. and reaction was further stirred for 2 h. Reaction was quenched with water (20 ml) and precipitate was filtered on and dried to give 120 mg of white solid as the product.

Workup

  1. customreaction
  2. temperatureto maintain
  3. customtemperature below 10° C. and reaction
  4. customReaction
  5. customwas quenched with water (20 ml) and precipitate
  6. filtrationwas filtered on and
  7. customdried

Sources & evidence

ORD record
ord-85080215b4344ba5be75eeada029153c
Source dataset
uspto-grants-2012_03
Patent number
US08129401B2

Reaction notes

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