1,3-Dichloroacetone → HCID 22726753, compound

HRID 2085975Notes

Reaction equation

HRID 2085975 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][NH:11][C:12]([NH2:14])=[S:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:15][CH2:16][C:17]([CH2:19]Cl)=O>C(O)C>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][NH:11][C:12]1[S:13][CH:19]=[C:17]([CH2:16][Cl:15])[N:14]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 107931,3-DichloroacetoneHCID 22726781HCID 22726781, compound

Product 1

HCID 22726753HCID 22726753, compoundYield 23.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of N-(2-t-butyloxycarbonylaminoethyl)thiourea (1.00 g, 4.54 mol) in ethanol (22 mL) was added 1,3-dichloroacetone (2.60 g, 20.47 mmol) at room temperature. After 2 hours the reaction mixture was concentrated under reduced pressure. The residue was triturated with ether and filtered to afford the solid precipitate of title product (1.40 g), which was used for next step without further purification. 1H NMR (CDCl3) δ 1.40 (s, 9H), 3.35 (m, 4H), 4.38 (s, 2H), 5.00 (br s, 1H), 6.40 (s, 1H).

Workup

  1. concentrationAfter 2 hours the reaction mixture was concentrated under reduced pressure
  2. customThe residue was triturated with ether
  3. filtrationfiltered

Sources & evidence

ORD record
ord-6192a5b8e10d41e3ad3c40181a190d7f
Source dataset
uspto-grants-2004_04
Patent number
US06723716B1

Reaction notes

Loading…