Sulfamic Acid → HCID 86679519, compound

HRID 1776563Notes

Reaction equation

HRID 1776563 reaction equation
[CH3:1][S:2]([O:5][C:6]1[CH:11]=[C:10]([CH:12]=[O:13])[CH:9]=[CH:8][C:7]=1[O:14][CH2:15][CH:16]1[CH2:18][CH2:17]1)(=[O:4])=[O:3].S(=O)(=O)([OH:21])N.Cl([O-])=O.[Na+]>C(O)(=O)C.O>[CH:16]1([CH2:15][O:14][C:7]2[CH:8]=[CH:9][C:10]([C:12]([OH:21])=[O:13])=[CH:11][C:6]=2[O:5][S:2]([CH3:1])(=[O:4])=[O:3])[CH2:17][CH2:18]1

Participants

6

Reactant 3

HCID 5987Sulfamic Acid2×HCID 23668197Sodium Chlorite2×HCID 86679518HCID 86679518, compound

Product 1

HCID 86679519HCID 86679519, compoundYield 87.1%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent3×

Conditions

Temperature
0 °C

Procedure

A mixture of 2-(cyclopropylmethoxy)-5-formylphenyl methanesulfonate (0.565 g, 2.090 mmol) and sulfamic acid (0.223 g, 2.299 mmol) in acetic acid (8 ml) was cooled to 0° C., and a solution of sodium chlorite (0.378 g, 4.18 mmol) in water (3 ml) was added. The resulting yellow mixture was allowed to warm to RT and stirred for 2 hours. Additional sulfamic acid (0.081 g, 0.836 mmol) and sodium chlorite (0.133 g, 1.463 mmol) in water (2 ml) were added over 1 hour. The reaction mixture was diluted with water (15 ml), and the precipitate was collected by filtration, washed with water and dried to obtain 4-(cyclopropylmethoxy)-3-(methylsulfonyloxy)benzoic acid (0.521 g, 1.820 mmol, 87% yield, MS/ESI+ 286.9 [MH]+). This product was employed in the next step without purification.

Workup

  1. temperatureto warm to RT
  2. filtrationthe precipitate was collected by filtration
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-3776811ee6c64e59bea810537db8ccac
Source dataset
uspto-grants-2016_02
Patent number
US09265768B2

Reaction notes

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