Sodium Hydroxide → HCID 18316453, compound

HRID 276310Notes

Reaction equation

HRID 276310 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]=[C:11]2[N:15]([CH2:16][C:17]([CH3:19])=[CH2:18])[CH2:14][CH2:13][S:12]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[OH-].[Na+]>OP(O)(O)=O.O>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([N:10]=[C:11]2[N:15]([CH:16]=[C:17]([CH3:19])[CH3:18])[CH2:14][CH2:13][S:12]2)=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 18316532HCID 18316532, compound

Product 1

HCID 18316453HCID 18316453, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1004Phosphoric AcidSolvent

Conditions

Temperature
80 °C

Procedure

2-Chloroethylammonium chloride (Entry 1) was reacted with 4-nitrophenyl isothiocyanate according to Method C1a to give 2-(4-nitrophenyl)-1,3-thiazolidine. The thiazolidine was reacted with 1-bromo-2-methyl-2-propene according to Method D2a to give 2-(4-nitrophenylimino)-3-(2-methylprop-2-en-1-yl)-1,3-thiazolidine. A mixture of 2-(4-nitrophenylimino)-3-(2-methylprop-2-en-1-yl)-1,3-thiazolidine (0.20 g) in poly(phosphoric acid) (0.4 mL) was heated at 80 ° C. for 5 h. The reaction mixture was then dissolved in 0 ° C. water (20 mL) with the aid of sonication. The aqueous mixture was adjusted to pH 12 with a 1N NaOH solution, then extracted with EtOAc (3×25 mL). The combined organic phases were dried (K2CO3) and concentrated under reduced pressure. The residue (0.21 g) was purified by preparative HPLC to afford 2-(4-nitrophenylimino)-3-(2-methylprop-1-en-1-yl)-1,3-thiazolidine.

Workup

  1. customwith the aid of sonication
  2. extractionextracted with EtOAc (3×25 mL)
  3. dry with materialThe combined organic phases were dried (K2CO3)
  4. concentrationconcentrated under reduced pressure
  5. customThe residue (0.21 g) was purified by preparative HPLC

Sources & evidence

ORD record
ord-da0e4f1a004444edb47a2e8a4b8b55c6
Source dataset
uspto-grants-2002_03
Patent number
US06353006B1

Reaction notes

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