Triethylamine → Coumate

HRID 1494017Notes

Reaction equation

HRID 1494017 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 3 M 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° C. 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° C. 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-f770ff5b16dc448a8fa0aa57fab29851
Source dataset
uspto-grants-1991_06
Patent number
US05025031

Reaction notes

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