Dichloromethane → 9H-9-fluorenyl-methyl-N-[(4-bromoanilino)carbothioyl]carbamate

HRID 432434Notes

Reaction equation

HRID 432434 reaction equation
[C:1]1([CH2:14][O:15][C:16]([N:18]=[C:19]=[S:20])=[O:17])[C:13]2[CH2:12][C:11]3C(=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[Br:21][C:22]1[CH:28]=[CH:27][C:25]([NH2:26])=[CH:24][CH:23]=1.Cl[CH2:30]Cl>>[CH:10]1[C:11]2[CH:14]([O:15][C:16](=[O:17])[N:18]([CH3:30])[C:19]([NH:26][C:25]3[CH:27]=[CH:28][C:22]([Br:21])=[CH:23][CH:24]=3)=[S:20])[C:1]3[C:13](=[CH:5][CH:4]=[CH:3][CH:2]=3)[C:12]=2[CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 3

HCID 6344Dichloromethane3×HCID 78074-BromoanilineHCID 22346806Fluorenylmethyloxycarbonyl isothiocyanate

Product 1

HCID 1317242539H-9-fluorenyl-methyl-N-[(4-bromoanilino)carbothioyl]carbamate

Conditions

Temperature
0 °C

Procedure

A solution of fluorenylmethyloxycarbonyl isothiocyanate (1.36 g, 4.84 mmol, Kearney, P. C.; Fernandez, M.; Flygare, J. A. J. Org. Chem. 1998, 63, 196-200) in dichloromethane (40 mL) was added via a pipet to a solution of 4-Bromoaniline (0.86 g, 5.00 mmol) in dichloromethane (10 mL) maintained at 0° C. and the resulting mixture stirred at ambient temperature for 14 h. The reaction was diluted with dichloromethane (60 mL) and washed with aqueous hydrochloric acid (0.5 M, 2×10 mL). The organic layer was dried (magnesium sulfate), filtered, and concentrated to afford the 9H-9-fluorenyl-methyl-N-[(4-bromoanilino)carbothioyl]carbamate (2.25 g, 4.97 mmol): RP-HPLC (25 to 100% acetonitrile in 0.1 M aqueous ammonium acetate over 10 min at 1 mL/min using a 5μ Hypersil HS C18, 250×4.6 mm column) Rt 14.25 min.

Workup

  1. washwashed with aqueous hydrochloric acid (0.5 M, 2×10 mL)
  2. dry with materialThe organic layer was dried (magnesium sulfate)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-3db9ad7e3bc74a979d3b2b86123d7f33
Source dataset
uspto-grants-2003_12
Patent number
US06660744B1

Reaction notes

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