Nitrogen → HCID 19824189, compound

HRID 728346Notes

Reaction equation

HRID 728346 reaction equation
[N:1]#N.[S:3]1[CH:7]=[CH:6][CH:5]=[C:4]1[C:8](Cl)=[O:9].Cl.N[C:13]1[CH:18]=[C:17]([CH:19]([CH3:21])[CH3:20])[C:16]([OH:22])=[C:15]([CH:23]([CH3:25])[CH3:24])[CH:14]=1.C(=O)([O-])O.[Na+]>C(Cl)Cl.O.C(OCC)(=O)C>[S:3]1[CH:7]=[CH:6][CH:5]=[C:4]1[C:8]([C:13]1[CH:18]=[C:17]([CH:19]([CH3:21])[CH3:20])[C:16]([OH:22])=[C:15]([CH:23]([CH3:25])[CH3:24])[C:14]=1[NH2:1])=[O:9]

Participants

8

Reactant 4

HCID 947NitrogenHCID 789282-Thiophenecarbonyl chlorideHCID 516892Sodium BicarbonateHCID 678336004-Amino-2,6-di(propan-2-yl)phenol--hydrogen chloride (1/1)

Product 1

HCID 19824189HCID 19824189, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Under ice-cooling and N2 atmosphere, a solution of 1.47 g of 2-thiophenecarbonyl chloride in 10 ml of methylene chloride is added to a mixture of 2.91 g of 4-amino-2,6-diisopropylphenol hydrochloride, 90 ml of ethyl acetate, 80 ml of water, and 8.0 g of sodium hydrogen carbonate during a period of 30 minutes. After stirring at room temperature for one hour, organic layer is separated, washed with water, 10 % HCl, water, dried, and concentrated. The obtained solid is recrystallized from chloroform-hexane to give 1.7 g of 4-(2-thienylcarbonyl)-amino-2,6-diisopropylphenol.

Workup

  1. temperatureUnder ice-cooling
  2. customorganic layer is separated
  3. washwashed with water, 10 % HCl, water
  4. customdried
  5. concentrationconcentrated
  6. customThe obtained solid is recrystallized from chloroform-hexane

Sources & evidence

ORD record
ord-4688d2b2495a47dc93bd0a8228707901
Source dataset
uspto-grants-1991_09
Patent number
US05047555

Reaction notes

Loading…