Triethylamine → N-carbomethoxy-N'-benzylsulfamoyl-O-methylisourea

HRID 246831Notes

Reaction equation

HRID 246831 reaction equation
[CH2:1]([NH:8][S:9](Cl)(=[O:11])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:13]([NH:17][C:18](=[NH:21])[O:19][CH3:20])([O:15][CH3:16])=[O:14].C(N(CC)CC)C>C1COCC1>[C:13]([NH:17][C:18](=[N:21][S:9](=[O:11])(=[O:10])[NH:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[O:19][CH3:20])([O:15][CH3:16])=[O:14]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13529095Benzylsulfamyl chlorideHCID 137319931Methyl N-(iminomethoxymethyl)carbamate

Product 1

HCID 70392213N-carbomethoxy-N'-benzylsulfamoyl-O-methylisourea

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of benzylsulfamoyl chloride (168 g) in anhydrous THF (300 ml) is added dropwise to a stirred solution of N-carbomethoxy-O-methylisourea (107 g) and triethylamine (90 g) in anhydrous THF (800 ml) under nitrogen at -70° C. The resulting suspension is warmed to RT, filtered and the filtrate evaporated in vacuo. The residue is partitioned between methylene chloride and 0.5N aq. HCl. The organic layer is dried, filtered, and concentrated in vacuo affording the desired product as an oil.

Workup

  1. filtrationfiltered
  2. customthe filtrate evaporated in vacuo
  3. customThe residue is partitioned between methylene chloride and 0.5N aq. HCl
  4. customThe organic layer is dried
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4099f6da5a8147cea0efd2977b40bde9
Source dataset
uspto-grants-1987_11
Patent number
US04704388

Reaction notes

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