3-(Dimethylamino)phenol → HCID 67854685, compound

HRID 327713Notes

Reaction equation

HRID 327713 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 (Preparation 21) 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 aqueous layers were back extracted with 1:1 ethyl acetate/acetonitrile once. The organic layers were combined, dried over sodium sulfate, charcoaled, filtered, and evaporated to a black oil weighing 7.57 g.

Workup

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

Sources & evidence

ORD record
ord-36a79514fd8b482c9f5eff206a998b12
Source dataset
uspto-grants-1993_12
Patent number
US05273993

Reaction notes

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