Carbon Tetrachloride → 2-[4-(N-benzyloxycarbonylamino)-2-nitronaphthalen-1-yl]ethyl chloride

HRID 431735Notes

Reaction equation

HRID 431735 reaction equation
[C:1]([Cl:5])(Cl)(Cl)Cl.[CH2:6]([O:13][C:14]([NH:16][C:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:20]([CH2:27]CO)=[C:19]([N+:30]([O-:32])=[O:31])[CH:18]=1)=[O:15])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C(Cl)Cl>[CH2:6]([O:13][C:14]([NH:16][C:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:20]([CH2:27][CH2:1][Cl:5])=[C:19]([N+:30]([O-:32])=[O:31])[CH:18]=1)=[O:15])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 5943Carbon TetrachlorideHCID 11776TriphenylphosphineHCID 187614142-[4-(N-benzyloxycarbonylamino)-2-nitronaphthalen-1-yl]ethanol

Product 1

HCID 187614502-[4-(N-benzyloxycarbonylamino)-2-nitronaphthalen-1-yl]ethyl chlorideYield 96.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

CCl4 (0.2 mL, 2.18 mmol) was added to a solution of 2-[4-(N-benzyloxycarbonylamino)-2-nitronaphthalen-1-yl]ethanol (0.1 g, 0.27 mmol) and Ph3P (0.29 g, 1.09 mmol) in CH2Cl2 (5 mL) under N2 atmosphere and stirred for 3 h. Flash chromatography (10% AcOEt-Petroleum ether) afforded of 2-[4-(N-benzyloxycarbonylamino)-2-nitronaphthalen-1-yl]ethyl chloride (0.1 g, 96%) as an orange solid. M.p. 122-124° C.; 1H NMR (CDCl3, 500 MHz) δ 8.18 (d, 8.5, 1H), 7.89 (d, 8.5, 1H), 7.70 (t, 7.0, 1H), 7.62 (t, 7.0, 1H), 7.45 (d, 7.0, 2H), 7.41 (t, 7.5, 2H), 7.35 (t, 7.5, 1H), 6.95 (s, 1H), 4.93 (brs, 1H), 4.51 (d, 5.0, 2H), 3.86 (t, 8.0, 2H), 3.56 (t, 8.5, 2H); IR (neat) 3087, 3033, 2927, 2856, 1594, 1519, 1439, 1342, 1124, 752, 699 cm−1. FABMS (NBA) m/z 340 (M−CO2+), ESMS m/z 341 (M−CO2+H+).

Sources & evidence

ORD record
ord-53d13a26cb874ac69b11974603addbc8
Source dataset
uspto-grants-2003_12
Patent number
US06660742B2

Reaction notes

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