3-(Dimethylamino)phenol → HCID 67854685, compound

HRID 1494025Notes

Reaction equation

HRID 1494025 reaction equation
[CH3:1][N:2]([CH3:10])[C:3]1[CH:4]=[C:5]([OH:9])[CH:6]=[CH:7][CH:8]=1.[S:11]([Cl:15])(=[O:14])(=[O:13])[NH2:12].C(N(CC)CC)C>C(#N)C.C(OCC)(=O)C>[ClH:15].[CH3:1][N:2]([CH3:10])[C:3]1[CH:4]=[C:5]([O:9][S:11](=[O:14])(=[O:13])[NH2:12])[CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 3

HCID 74213-(Dimethylamino)phenolHCID 8471TriethylamineHCID 24499Chlorosulfamic acid

Product 1

HCID 67854685HCID 67854685, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
15 °C

Procedure

A solution of 3-dimethylaminophenol (6.90 g, 0.05 mole) in 30 ml of acetonitrile was added in 13 minutes to a chilled (15° C.) stirred solution of 0.10 mole sulfamoyl chloride in 30 ml of acetonitrile. This was followed by the addition of 14 ml (0.10 mole) of triethylamine. The resultant mixture was stirred at room temperature overnight. The reaction was diluted with ethyl acetate (~60 ml) and then extracted twice with sodium bicarbonate solution. The combined aqueous layers were back extracted with 1:1 ethyl acetate/acetonitrile once. The organic layers were combined, dried over sodium sulfate, treated with charcoal, filtered, and evaporated to a black oil weighing 7.57 g.

Workup

  1. extractionextracted twice with sodium bicarbonate solution
  2. extractionThe combined aqueous layers were back extracted with 1:1 ethyl acetate/acetonitrile once
  3. dry with materialdried over sodium sulfate
  4. additiontreated with charcoal
  5. filtrationfiltered
  6. customevaporated to a black oil

Sources & evidence

ORD record
ord-fa0b5556fa294080a798f6406c1c8658
Source dataset
uspto-grants-1991_06
Patent number
US05025031

Reaction notes

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