1,3-Dichloroacetone → (4-Chloromethyl-thiazol-2-yl)-naphthalen-1-yl-amine

HRID 857080Notes

Reaction equation

HRID 857080 reaction equation
[C:1]1([NH:11][C:12]([NH2:14])=[S:13])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[Cl:15][CH2:16][C:17]([CH2:19]Cl)=O>CC(C)=O>[Cl:15][CH2:16][C:17]1[N:14]=[C:12]([NH:11][C:1]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH:4]=[CH:3][CH:2]=2)[S:13][CH:19]=1

Participants

4

Reactant 2

HCID 107931,3-DichloroacetoneHCID 736366Alpha-Naphthylthiourea

Product 1

HCID 21866567(4-Chloromethyl-thiazol-2-yl)-naphthalen-1-yl-amine

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of naphthalen-1-yl-thiourea (iii) (2.02 g, 10 mmol) in acetone (50 mL) at room temperature was added 1,3-dichloroacetone (1.03 g, 10.5 mmol). The reaction mixture was stirred at room temperature overnight. The reaction mixture was filtered and washed with methanol. The filtrate was treated with hexane to afford a white precipitate. The precipitate was filtered and washed with hexane.

Workup

  1. filtrationThe reaction mixture was filtered
  2. washwashed with methanol
  3. additionThe filtrate was treated with hexane
  4. customto afford a white precipitate
  5. filtrationThe precipitate was filtered
  6. washwashed with hexane

Sources & evidence

ORD record
ord-01f4098aa1b34fafbb1a2eada84a92d2
Source dataset
uspto-grants-2006_12
Patent number
US07144903B2

Reaction notes

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