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4-Bromo-2-chloro-1-isocyanatobenzene → 3-(4-bromo-2-chlorophenyl)-1-[(4S,5S)-2,2-dimethyl-4-phenyl-1,3-dioxan-5-yl]urea

HRID 966069
Notes
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Reaction equation

HRID 966069 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.[Br:16][C:17]1[CH:22]=[CH:21][C:20]([N:23]=[C:24]=[O:25])=[C:19]([Cl:26])[CH:18]=1>CCCCC.ClCCl>[Br:16][C:17]1[CH:22]=[CH:21][C:20]([NH:23][C:24]([NH:14][C@H:5]2[CH2:4][O:3][C:2]([CH3:15])([CH3:1])[O:7][C@H:6]2[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:25])=[C:19]([Cl:26])[CH:18]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 27333634-Bromo-2-chloro-1-isocyanatobenzeneHCID 7061833(4S,5S)-2,2-dimethyl-4-phenyl-1,3-dioxan-5-amine

Product 1

HCID 100488623-(4-bromo-2-chlorophenyl)-1-[(4S,5S)-2,2-dimethyl-4-phenyl-1,3-dioxan-5-yl]ureaYield 88%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8003Pentane
Solvent

Procedure

To a stirred or shaken solution of 157 mg (0.76 mmol) of (4S,5S)-2,2-dimethyl-4-phenyl-1,3-dioxan-5-amine (abbreviated as (4S,5S)-amine 1) in pentane (3.5 mL) was added dropwise a solution of 169 mg (0.73 mmol) of 4-bromo-2-chlorophenyl isocyanate in dichloromethane (0.7 mL). A white precipitate was observed after stirring for 0.5 to 2 h. The precipitate was collected, rinsed with pentane, and dried under vacuum to yield 280 mg (88%) of the title compound. In some examples, pentane was used to dissolve the required isocyanate rather than dichloromethane. In addition, if the required isocyanate was a liquid, it was added dropwise as a neat liquid on small-scale reactions such as this. In cases where a precipitate was not observed or the precipitate was not of sufficient purity, the solvent was evaporated, and the residue was purified by column chromatography (hexanes/ethyl acetate) to yield the desired product.

Workup

  1. stirringafter stirring for 0.5 to 2 h
  2. customThe precipitate was collected
  3. washrinsed with pentane
  4. customdried under vacuum

Sources & evidence

ORD record
ord-83c5b75823eb48ad9d5db2ebb9d76da3
Source dataset
uspto-grants-2005_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06951882B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes