p-Aminoacetophenone → HCID 21416951, compound

HRID 442255Notes

Reaction equation

HRID 442255 reaction equation
[CH3:1][NH:2][S:3](Cl)(=[O:5])=[O:4].C(N(CC)CC)C.[NH2:14][C:15]1[CH:20]=[CH:19][C:18]([C:21](=[O:23])[CH3:22])=[CH:17][CH:16]=1.Cl.C(N(CC)CC)C>CCOCC>[C:21]([C:18]1[CH:19]=[CH:20][C:15]([NH:14][S:3]([NH:2][CH3:1])(=[O:5])=[O:4])=[CH:16][CH:17]=1)(=[O:23])[CH3:22]

Participants

6

Reactant 4

HCID 7468p-AminoacetophenoneHCID 8471TriethylamineHCID 11130Triethylamine hydrochlorideHCID 11789235N-Methylsulfamoyl chloride

Product 1

HCID 21416951HCID 21416951, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
-50 °C

Procedure

Methylsulfamoyl chloride (42.5 g., 0.33 mole) is added dropwise to a mixture of triethylamine (33.4 g., 0.33 mole) and p-aminoacetophenone (40.5 g., 0.30 mole )in ether (1.5 1.) at -50° C. The mixture is stirred at -50° C. and then allowed to warm to -10° C. The mixture is filtered to give a mixture of product and triethylamine hydrochloride. Washing with water and recrystallization from isopropanol furnishes 30.6 g. (40%) of the above pure intermediate, m.p. 159°-159.5° C. (dec.).

Workup

  1. customat -50° C
  2. temperatureto warm to -10° C
  3. filtrationThe mixture is filtered
  4. customto give
  5. washWashing with water and recrystallization from isopropanol
  6. customfurnishes 30.6 g

Sources & evidence

ORD record
ord-ed29ff02e6de48b3b4469b34aa1975b6
Source dataset
uspto-grants-1977_08
Patent number
US04044151

Reaction notes

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