N,N-Diphenylcarbamic chloride → HCID 70186186, compound

HRID 344059Notes

Reaction equation

[OH:1][CH2:2][CH2:3][CH:4]1[CH2:13][CH2:12][C:11]2[C:10]([O:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:9][CH:8]=[CH:7][C:6]=2[CH2:5]1.[C:21]1([N:27]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:28](Cl)=[O:29])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>N1C=CC=CC=1>[C:21]1([N:27]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:28](=[O:29])[O:1][CH2:2][CH2:3][CH:4]2[CH2:13][CH2:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][C:10]=3[O:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:5]2)[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of ethyl [5,6,7,8-tetrahydro-6-(2-hydroxyethyl)-1-naphthyloxy]acetate (50 mg), N,N-diphenylcarbamoyl chloride (50 mg), and pyridine (32 mg) was stirred at 100° C. for 1 hour and 40 minutes, cooled to room temperature, and partitioned between ethyl acetate and 1N hydrochloric acid. The ethyl acetate layer was washed successively with water, aqueous sodium bicarbonate, and brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was chromatographed (toluene-ethyl acetate) over silica gel to afford 2-[5-(ethoxycarbonylmethoxy)-1,2,3,4-tetrahydro-2-naphthyl]ethyl N,N-diphenylcarbamate (31 mg) as a syrup.

Workup

temperaturecooled to room temperature
custompartitioned between ethyl acetate and 1N hydrochloric acid
washThe ethyl acetate layer was washed successively with water, aqueous sodium bicarbonate, and brine
dry with materialdried over magnesium sulfate
customevaporated in vacuo
customThe residue was chromatographed (toluene-ethyl acetate) over silica gel

Sources & evidence

ORD record: ord-d5a8dc664e7e4cd6a478167c36ef5fdd
Source dataset: uspto-grants-1999_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05863918

Reaction notes

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