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1,3-Dichloro-2-isothiocyanatobenzene → 2-(2,6-Dichlorophenylimino)-3-cyclohexyl-4,4-dimethyl-1,3-thiazolidine

HRID 276287
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HRID 276287 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[N:9]=[C:10]=[S:11].[CH:12]1([NH:18][C:19]([CH3:23])([CH3:22])[CH2:20][OH:21])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1>C(Cl)Cl>[CH:12]1([NH:18][C:19]([CH3:23])([CH3:22])[CH2:20][OH:21])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1.[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[N:9]=[C:10]1[N:18]([CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)[C:19]([CH3:23])([CH3:22])[CH2:20][S:11]1
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참가 물질

5

반응물 2

HCID 1232391,3-Dichloro-2-isothiocyanatobenzeneHCID 277599N-Cyclohexyl-1,1-dimethyl-2-hydroxyethanamine

생성물 2

HCID 277599N-Cyclohexyl-1,1-dimethyl-2-hydroxyethanamineHCID 183161792-(2,6-Dichlorophenylimino)-3-cyclohexyl-4,4-dimethyl-1,3-thiazolidine수율 65.3%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

N-Cyclohexyl-1,1-dimethyl-2-hydroxyethanamine was prepared in a manner analogous to Method B4a. A solution of 2,6-dichlorophenyl isothiocyanate (1.2 g, 6.0 mmol) and N-cyclohexyl-1,1-dimethyl-2-hydroxyethanamine (1.0 g, 6.0 mmol) in CH2Cl2 (10 mL) was stirred for 20 h at room temp. The resulting mixture was concentrated under reduced pressure, then treated with a 33% HCl solution (15 mL). The resulting mixture was heated at the reflux temp. for 1 h, cooled to room temp. and neutralized with a 45% NaOH solution. The resulting slurry was filtered, and the resulting solids were washed with water (20 mL), then recrystallized (EtOH) to yield 2-(2,6-dichlorophenylimino)-3-cyclohexyl-4,4-dimethyl-1,3-thiazolidine (0.70 g, 33%/o): mp 134° C. When appropriate, the product was converted into the HCl salt by dissolving the free base (5 mmol) in Et2O (50 mL) and treating this solution with a 2N ethereal HCl solution until no more solid precipitated. The resulting slurry was filtered and the resulting solids were washed with Et2O (25 mL) followed by EtOAc (25 mL).

후처리

  1. concentrationThe resulting mixture was concentrated under reduced pressure
  2. additiontreated with a 33% HCl solution (15 mL)
  3. temperatureThe resulting mixture was heated at the reflux temp
  4. temperaturecooled to room temp.
  5. filtrationThe resulting slurry was filtered
  6. washthe resulting solids were washed with water (20 mL)
  7. customrecrystallized (EtOH)

출처 및 근거

ORD 기록
ord-c9c145cf06f64feabc107217a566f25c
출처 데이터셋
uspto-grants-2002_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06353006B1

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