Carzenide → Methyl 4-sulphamoylbenzoate

HRID 2086143Notes

Reaction equation

HRID 2086143 reaction equation
[OH-].[K+].[CH3:3]N(N=O)/C(/N)=N/[N+]([O-])=O.[S:13]([C:17]1[CH:25]=[CH:24][C:20]([C:21]([OH:23])=[O:22])=[CH:19][CH:18]=1)(=[O:16])(=[O:15])[NH2:14]>O.CCOCC>[CH3:3][O:22][C:21](=[O:23])[C:20]1[CH:19]=[CH:18][C:17]([S:13](=[O:15])(=[O:16])[NH2:14])=[CH:25][CH:24]=1

Participants

6

Reactant 3

HCID 8739CarzenideHCID 14797Potassium HydroxideHCID 95620601-Methyl-2-nitro-1-nitrosoguanidine

Product 1

HCID 89847Methyl 4-sulphamoylbenzoate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of KOH (108 mg, 2.0 mmol) in water (1 mL) was added Et2O and cooled to 0° C. MNNG (292 mg, 1.99 mmol) was added and the resulting yellow solution was added to a suspension of 4-Sulfamoyl-benzoic acid in Et2O at room temperature and stirred overnight. The reaction was quenched with acetic acid and the resulting mixture was diluted with water. The mixture was then extracted with ethyl acetate and the combined organic extracts was washed with bine and dried over Na2SO4. Removal of solvent gave the crude product which was used in the next reaction without further purification. 1H NMR (400 MHz, MeOD) δ8.17 (d, 2H), 8.00 (d, 2H), 3.92 (s, 3H).

Workup

  1. customThe reaction was quenched with acetic acid
  2. additionthe resulting mixture was diluted with water
  3. extractionThe mixture was then extracted with ethyl acetate
  4. washthe combined organic extracts was washed with bine
  5. dry with materialdried over Na2SO4
  6. customRemoval of solvent

Sources & evidence

ORD record
ord-5970e2066aae4df6915ec034610f9e38
Source dataset
uspto-grants-2004_04
Patent number
US06723749B2

Reaction notes

Loading…