2,4-Dichloro-1-isothiocyanatobenzene → 1-(2,4-Dichloro-phenyl)-3-((4S,5S)-2,2-dimethyl-4-phenyl-[1,3]dioxan-5-yl)-thiourea

HRID 966076Notes

Reaction equation

HRID 966076 reaction equation
[CH3:1][C:2]1([CH3:15])[O:7][C@@H:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C@@H:5]([NH2:14])[CH2:4][O:3]1.[Cl:16][C:17]1[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:18]=1[N:24]=[C:25]=[S:26]>CCCCC.ClCCl>[Cl:16][C:17]1[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:18]=1[NH:24][C:25]([NH:14][C@H:5]1[CH2:4][O:3][C:2]([CH3:15])([CH3:1])[O:7][C@H:6]1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[S:26]

Participants

5

Reactant 2

HCID 810662,4-Dichloro-1-isothiocyanatobenzeneHCID 7061833(4S,5S)-2,2-dimethyl-4-phenyl-1,3-dioxan-5-amine

Product 1

HCID 443933371-(2,4-Dichloro-phenyl)-3-((4S,5S)-2,2-dimethyl-4-phenyl-[1,3]dioxan-5-yl)-thioureaYield 67.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8003PentaneSolvent

Procedure

To a solution of 130 mg (0.62 mmol) of (4S,5S)-amine 1 in pentane (2.0 mL) was added dropwise a solution of 116 mg (0.62 mmol) of 2,4-dichlorophenyl isothiocyanate in dichloromethane (0.15 mL). After stirring for ˜24 h, a white precipitate was collected, rinsed with pentane, and dried under reduced pressure to yield 172 mg (67%) of the title compound.

Workup

  1. customa white precipitate was collected
  2. washrinsed with pentane
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-9ffb4a9c06ee4a3a9191efb84fd7a692
Source dataset
uspto-grants-2005_10
Patent number
US06951882B2

Reaction notes

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