Chlorosulfamic acid → Sulfamic acid 2-[4-(1H-1,2,4-triazol-1-yl)phenoxy]ethyl ester

HRID 327733Notes

Reaction equation

HRID 327733 reaction equation
[N:1]1([C:6]2[CH:15]=[CH:14][C:9]([O:10][CH2:11][CH2:12][OH:13])=[CH:8][CH:7]=2)[CH:5]=[N:4][CH:3]=[N:2]1.[S:16](Cl)(=[O:19])(=[O:18])[NH2:17].C(N(C(C)C)CC)(C)C>C(#N)C>[N:1]1([C:6]2[CH:7]=[CH:8][C:9]([O:10][CH2:11][CH2:12][O:13][S:16](=[O:19])(=[O:18])[NH2:17])=[CH:14][CH:15]=2)[CH:5]=[N:4][CH:3]=[N:2]1

Participants

5

Reactant 3

HCID 24499Chlorosulfamic acidHCID 81531DiisopropylethylamineHCID 191086732-[4-(1H-1,2,4-Triazol-1-yl)phenoxy]ethanol

Product 1

HCID 54444078Sulfamic acid 2-[4-(1H-1,2,4-triazol-1-yl)phenoxy]ethyl esterYield 55%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A solution of 8.2 g (0.04 mole) of 2-[4-(1H-1,2,4-triazol-1-yl)phenoxyl]ethanol in 100 ml of acetonitrile was treated with a solution of 1.3 equivalents of sulfamoyl chloride in 19 ml of acetonitrile. One equivalent, 5.2 g (0.04 mole) of diisopropylethylamine was also added in one portion. The mixture was stirred for 2 hr. The precipitate was collected and partitioned between ethyl acetate and a dilute potassium carbonate solution. The organic layer was separated and concentrated to a white powder. The powder was triturated with ethyl ether, collected and dried to give 6.3 g (55%) of white powder, mp 134°-136° C.

Workup

  1. customThe precipitate was collected
  2. custompartitioned between ethyl acetate
  3. customThe organic layer was separated
  4. concentrationconcentrated to a white powder
  5. customThe powder was triturated with ethyl ether
  6. customcollected
  7. customdried

Sources & evidence

ORD record
ord-9fc6ea07ebc14716ae48ef41d30a0344
Source dataset
uspto-grants-1993_12
Patent number
US05273993

Reaction notes

Loading…