Ethanolamine → 8-(2-hydroxyethylsulfamyl)-3-methyl-4-oxo-2-phenyl-4H-1-benzopyran

HRID 1653805Notes

Reaction equation

HRID 1653805 reaction equation
[CH3:1][C:2]1[C:7](=[O:8])[C:6]2[CH:9]=[CH:10][CH:11]=[C:12]([S:13](Cl)(=[O:15])=[O:14])[C:5]=2[O:4][C:3]=1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[CH2:23]([CH2:25][NH2:26])[OH:24].C(N(CC)CC)C.O>O1CCCC1>[OH:24][CH2:23][CH2:25][NH:26][S:13]([C:12]1[C:5]2[O:4][C:3]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[C:2]([CH3:1])[C:7](=[O:8])[C:6]=2[CH:9]=[CH:10][CH:11]=1)(=[O:15])=[O:14]

Participants

6

Reactant 4

HCID 700EthanolamineHCID 962WaterHCID 8471TriethylamineHCID 199727993-methyl-4-oxo-2-phenyl-4H-1-benzopyran-8-sulfonyl chloride

Product 1

HCID 199727788-(2-hydroxyethylsulfamyl)-3-methyl-4-oxo-2-phenyl-4H-1-benzopyran

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 5 g of Intermediate VIII in 37 ml of tetrahydrofuran was added dropwise at 0° C. to a mixture of 2.5 ml of ethanolamine and 2.5 ml of triethylamine in 25 ml of tetrahydrofuran. After stirring at 20°-25° C., the reaction mixture was poured into 400 ml of water. A precipitate formed, and was collected by suction filtration, washed with water and air dried, yielding 4.6 g of 8-(2-hydroxyethylsulfamyl)-3-methyl-4-oxo-2-phenyl-4H-1-benzopyran, melting at 186°-187° C. after crystallization from ethyl acetate.

Workup

  1. customA precipitate formed
  2. filtrationwas collected by suction filtration
  3. washwashed with water and air
  4. customdried

Sources & evidence

ORD record
ord-5a94344d53aa4b6cbc4152e9d1b4c144
Source dataset
uspto-grants-1995_04
Patent number
US05403842

Reaction notes

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