Triethylamine → Coumate

HRID 1613786Notes

Reaction equation

HRID 1613786 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([CH3:13])=[CH:7][C:8](=[O:12])[O:9]2)=[CH:4][CH:3]=1.[S:14](Cl)(=[O:17])(=[O:16])[NH2:15].C(N(CC)CC)C>C(#N)C>[CH3:13][C:6]1[C:5]2[CH:4]=[CH:3][C:2]([O:1][S:14](=[O:17])(=[O:16])[NH2:15])=[CH:11][C:10]=2[O:9][C:8](=[O:12])[CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 24499Chlorosulfamic acidHCID 52805674-Methylumbelliferone

Product 1

HCID 9859866CoumateYield 41.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A slurry of 7-hydroxy-4-methylcoumarin (17.6 g, 0.10 mole) in acetonitrile (100 ml) was treated with a total of 84 ml of 3M sulfamoyl chloride (0.255 mole) in acetonitrile. The mixture was then treated dropwise with triethylamine (25.8 g, 0.255 mole). The reaction temperature was allowed to rise to 45° without any cooling. The mixture was stirred overnight at ambient temperature. The precipitate was collected, triturated with water, and dried in a vacuum oven at 70° C. for 15 hr to give 10.5 g (41%) of white powder, mp 161°-164° C.

Workup

  1. customto rise to 45° without any cooling
  2. customThe precipitate was collected
  3. customtriturated with water
  4. customdried in a vacuum oven at 70° C. for 15 hr

Sources & evidence

ORD record
ord-626cd38e37d4499f901cda7c0758e833
Source dataset
uspto-grants-1993_03
Patent number
US05194446

Reaction notes

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