Phosgene → HCID 11484465, compound

HRID 1760843Notes

Reaction equation

HRID 1760843 reaction equation
[CH2:1]([NH:6][C:7]1[CH:16]=[CH:15][C:14]2[C:13]([CH3:18])([CH3:17])[CH2:12][CH2:11][C:10]([CH3:20])([CH3:19])[C:9]=2[CH:8]=1)[CH2:2][CH2:3][CH2:4][CH3:5].[C:21](Cl)([Cl:23])=[O:22]>C1(C)C=CC=CC=1>[CH2:1]([N:6]([C:7]1[CH:16]=[CH:15][C:14]2[C:13]([CH3:18])([CH3:17])[CH2:12][CH2:11][C:10]([CH3:19])([CH3:20])[C:9]=2[CH:8]=1)[C:21]([Cl:23])=[O:22])[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

4

Reactant 2

HCID 6371PhosgeneHCID 11208062HCID 11208062, compound

Product 1

HCID 11484465HCID 11484465, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A solution of pentyl-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-amine (51) (390 mg, 1.45 mmole) in 6 mL toluene was treated with 0.9 mL of a 20% phosgene solution in toluene and stirred at room temperature for 12 hours. The reaction mixture was concentrated in vacuo to give pentyl-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-carbamoyl chloride as a pale yellow solid. The solid was dissolved in 5 mL pyridine, treated with 0.5 g of methyl 4-amino-3-fluorobenzoate and stirred at 40° C. for three days. Volatile material was removed in vacuo and the residue subjected to flash chromatography (SiO2, 20% ethyl acetate/hexanes), yielding 17 mg of methyl 3-fluoro-4-[3-pentyl-3-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-ureido]-benzoate.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-59cc5a2c97b04e5383add60f0bea8454
Source dataset
uspto-grants-2005_01
Patent number
US06844466B2

Reaction notes

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