Chlorosulfamic acid → HCID 54170068, compound

HRID 327700Notes

Reaction equation

HRID 327700 reaction equation
[OH:1][C:2]1[C:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:5][S:4][N:3]=1.[S:13](Cl)(=[O:16])(=[O:15])[NH2:14].C(N(C(C)C)CC)(C)C>C(#N)C>[C:7]1([C:6]2[C:2]([O:1][S:13](=[O:16])(=[O:15])[NH2:14])=[N:3][S:4][N:5]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 24499Chlorosulfamic acidHCID 81531DiisopropylethylamineHCID 178519020HCID 178519020, compound

Product 1

HCID 54170068HCID 54170068, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A slurry of 3-hydroxy-4-phenyl-1,2,5-thiadiazole (15.0 g, 0.084 mole) in acetonitrile (100 ml) was treated by the simultaneous dropwise addition of a sulfamoyl chloride solution in acetonitrile (0.20 mole, 66 ml of 3M) and a diisopropylethylamine solution (0.22 mole in enough 1:1 acetonitrile/methylene chloride to make 66 ml). High Pressure Liquid Chromatography analysis indicated a maximum of 85% conversion of starting material to product. The reaction was worked up by concentration of the reaction mixture and partitioning the residue between ethyl ether and water. Concentration of the ether fraction gave a white paste from which desired product was separated by dissolving in a small amount of acetonitrile. The product was crystallized from the acetonitrile to give 2.8 g (13%) of the title compound as a white powder, mp 128°-130° C.

Workup

  1. custompartitioning the residue between ethyl ether and water

Sources & evidence

ORD record
ord-7862eb4f24d445e19ac37606135d911e
Source dataset
uspto-grants-1993_12
Patent number
US05273993

Reaction notes

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