Dimethylformamide → [5-(3-Azidopropoxy)-2-nitrophenyl]methanol

HRID 1048735Notes

Reaction equation

CN(C=O)C.Cl[CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:12]=[CH:13][C:14]([N+:19]([O-:21])=[O:20])=[C:15]([CH2:17][OH:18])[CH:16]=1.[N-:22]=[N+:23]=[N-:24].[Na+]>C(OCC)(=O)C>[N:22]([CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:12]=[CH:13][C:14]([N+:19]([O-:21])=[O:20])=[C:15]([CH2:17][OH:18])[CH:16]=1)=[N+:23]=[N-:24]

Participants

Conditions

Temperature: 70 °C

Procedure

DMF (7.5 mL) was added to (5-(3-chloropropoxy)-2-nitrophenyl)methanol (635 mg, 0.00258 moles) and sodium azide (252 mg, 0.00387 moles) in a flask, and the resulting mixture was heated to 70° C. and stirred overnight. The reaction was diluted in ethyl acetate (100 mL) and washed twice with water (75 mL each) and once with brine (75 mL). The organic layer was dried with anhydrous magnesium sulfate, which was filtered out. The filtrate was concentrated on a rotary evaporator and dried in vacuo overnight to yield (5-(3-azidopropoxy)-2-nitrophenyl)methanol as a yellow solid (yield 88%). H NMR (400 MHz, CD2Cl2) δ 8.16 (d, J=9.1 Hz, 1H), 7.27 (d, J=2.8 Hz, 1H), 6.91 (dd, J=9.1, 2.8 Hz, 1H), 4.98 (s, 2H), 4.18 (t, J=6.0 Hz, 2H), 3.53 (t, J=6.6 Hz, 2H), 2.12-2.06 (m, 2H). 13C-NMR (100 MHz, CD2Cl2) δ 163.99, 141.22, 128.43, 114.97, 113.93, 66.15, 63.26, 48.68, 29.13 HRMS m/z: calculated for C10H12N4O4 [M+H]+, 253.0931. found, 253.0939.

Workup

washwashed twice with water (75 mL each) and once with brine (75 mL)
dry with materialThe organic layer was dried with anhydrous magnesium sulfate, which
filtrationwas filtered out
concentrationThe filtrate was concentrated on a rotary evaporator
customdried in vacuo overnight

Sources & evidence

ORD record: ord-693a2494d2a64d6e84f87595007867e9
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09381253B2

Reaction notes

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