N,N-Diphenylcarbamic chloride → (1,2,3,4-tetrahydro-5-methoxy-2-naphthyl)methyl N,N-diphenylcarbamate

HRID 963692Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][CH2:6][CH:7]([CH2:13][OH:14])[CH2:8]2.[C:15]1([N:21]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:22](Cl)=[O:23])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>N1C=CC=CC=1>[C:15]1([N:21]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:22](=[O:23])[O:14][CH2:13][CH:7]2[CH2:6][CH2:5][C:4]3[C:9](=[CH:10][CH:11]=[CH:12][C:3]=3[O:2][CH3:1])[CH2:8]2)[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of (1,2,3,4-tetrahydro-5-methoxy-2-naphthyl)methanol (192 mg) and N,N-diphenylcarbamoyl chloride (348 mg) in pyridine (180 mg) was stirred at 100° C. for 2 hours, cooled to room temperature, and partitioned between ethyl acetate and 1N hydrochloric acid. The organic layer was washed successively with brine, aqueous sodium bicarbonate and brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was triturated with diethyl ether to afford (1,2,3,4-tetrahydro-5-methoxy-2-naphthyl)methyl N,N-diphenylcarbamate (218 mg) as a pale purple powder. mp: 143.5°-146° C.

Workup

temperaturecooled to room temperature
custompartitioned between ethyl acetate and 1N hydrochloric acid
washThe organic layer was washed successively with brine, aqueous sodium bicarbonate and brine
dry with materialdried over magnesium sulfate
customevaporated in vacuo
customThe residue was triturated with diethyl ether

Sources & evidence

ORD record: ord-a965fa2ed1324f32a4755d56a4d7fab9
Source dataset: uspto-grants-1998_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05763489

Reaction notes

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