Sulfamic Acid → HCID 66610949, compound

HRID 2204715Notes

Reaction equation

HRID 2204715 reaction equation
[Cl:1][C:2]1[C:3]([CH:26]=[O:27])=[CH:4][C:5]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[C:6]([CH:17]=1)[C:7]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8].CC(CC)=C.S(=O)(=O)([OH:35])N.Cl([O-])=O.[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>O1CCCC1.O.CS(C)=O>[Cl:1][C:2]1[CH:17]=[C:6]([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])[C:5]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:4][C:3]=1[C:26]([OH:35])=[O:27]

Participants

9

Reactant 5

HCID 5987Sulfamic AcidHCID 112402-Methyl-1-buteneHCID 24477Sodium ThiosulfateHCID 23668197Sodium ChloriteHCID 86694931HCID 86694931, compound

Product 1

HCID 66610949HCID 66610949, compound

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of phenylmethyl 5-chloro-4-formyl-2-[(phenylmethyl)oxy]benzoate (may be prepared as described in Description 62; 1.4 g, 3.68 mmol) in tetrahydrofuran (8 ml) was added dimethyl sulfoxide (0.8 ml) and 2-methyl-1-butene (0.79 ml, 7.35 mmol), and sulfamic acid (1.21 g, 12.50 mmol). The solution was cooled to 0° C. and sodium chlorite (1.00 g, 11.03 mmol) in water (8 ml) was added. The mixture was stirred for one hour, then saturated sodium thiosulfate solution was added (15 ml) and the mixture was stirred for another 10 minutes, The mixture was extracted with ethyl acetate (3×20 ml) and the organic layer was washed with water (10 ml) and 2M HCl (10 ml), dried (MgSO4) and the solvent removed in vacuo to give the title compound as an off white solid. 1.46 g.

Workup

  1. stirringthe mixture was stirred for another 10 minutes
  2. extractionThe mixture was extracted with ethyl acetate (3×20 ml)
  3. washthe organic layer was washed with water (10 ml) and 2M HCl (10 ml)
  4. dry with materialdried (MgSO4)
  5. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-2338bfe900a44dea9056417c36f8ce97
Source dataset
uspto-grants-2016_06
Patent number
US09365551B2

Reaction notes

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