Trichloroacetonitrile → (4-Bromophenyl)(thien-3-yl)methyl 2,2,2-trichloroethammidoate

HRID 1180388Notes

Reaction equation

HRID 1180388 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:10]2[CH:14]=[CH:13][S:12][CH:11]=2)[OH:9])=[CH:4][CH:3]=1.[H-].[Na+].[Cl:17][C:18]([Cl:22])([Cl:21])[C:19]#[N:20]>C(OCC)C>[Cl:17][C:18]([Cl:22])([Cl:21])[C:19](=[NH:20])[O:9][CH:8]([C:5]1[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][CH:6]=1)[C:10]1[CH:14]=[CH:13][S:12][CH:11]=1

Participants

5

Reactant 3

HCID 11011TrichloroacetonitrileHCID 24758Sodium hydrideHCID 49962536(4-Bromophenyl)(thiophen-3-yl)methanol

Product 1

HCID 69473113(4-Bromophenyl)(thien-3-yl)methyl 2,2,2-trichloroethammidoate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of (4-bromophenyl)(thien-3-yl)methanol from step 1 (632 mg, 2.36 mmol) in diethyl ether (2.5 mL) at 0° C. was added sodium hydride (6 mg, 0.24 mmol). Then trichloroacetonitrile was added dropwise (237 μL, 2.36 mmol) over 15 minutes and the reaction was allowed to warm to room temperature for 3 hours. The reaction was then filtered over celite and concentrated under reduced pressure. The resulting crude compound was used as such in the next step.

Workup

  1. filtrationThe reaction was then filtered over celite and
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-75e5a14f24f343bbb1f14ea62e29a683
Source dataset
uspto-grants-2007_10
Patent number
US07279478B2

Reaction notes

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