Triethylamine → HCID 22096740, compound

HRID 1729081Notes

Reaction equation

[CH2:1]([N:3]([CH2:13][CH2:14]O)[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([N+:10]([O-:12])=[O:11])[CH:5]=1)[CH3:2].CCN(CC)CC.CS([Cl:27])(=O)=O.[Li+].[Cl-]>C(Cl)Cl.CN(C=O)C>[Cl:27][CH2:14][CH2:13][N:3]([CH2:1][CH3:2])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([N+:10]([O-:12])=[O:11])[CH:5]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A stirred solution of the above alcohol (XI; R=H) (4.0 g, 19 mmol) in CH2Cl2 (35 mL) containing NEt3 (2.91 mL, 21 mmol) was treated dropwise at 0 ° C. with methanesulfonylchloride (1.62 mL, 21 mmol). After being stirred at 0 ° C. for a further 30 min and at20 ° C. for 30 min, the reaction mixture was diluted with CH2Cl2 (35 mL) and washed successively with 1N HCl, 1N Na2CO3and saturated NaCl, and worked up to give the crude mesylate, which was immediately treated with LiCl (2 g) in dry DMF (20 mL) at 75° C. for 30 min. Removal of excess solvent under reduced pressure, and chromatography of the residue on SiO2 (EtOAc/petroleum ether, 1:4 ) gave N-(2-chloroethyl)-N-ethyl-3-nitroaniline (XII; R=H) (3.58 g, 82%)as yellow prisms, mp (petroleum ether) 56°-57 ° C. 1H NMR (CDCl3) 7.51 (dd, J=7.9, 1.9 Hz, 1 H, H-4), 7.48 (t, j=2.4 Hz, 1 H, H-2), 7.32 (m, 2 H, H-5), 6.95 (dd, J=8.4, 2.7 Hz, H-6), 3.70 (m, 2 H, NCH2CH2Cl), 3.64 (m, 2 H, CH2Cl), 3.50 (q, J=7.1 Hz, 2 H, NCH2CH3), 1.22 (t, J=7.1 Hz, 3 H, CH3). Anal.(C10H13ClN2O2) C,H,N,Cl.

Workup

waitfor 30 min
washwashed successively with 1N HCl, 1N Na2CO3and saturated NaCl
customto give the crude mesylate, which
customRemoval of excess solvent under reduced pressure, and chromatography of the residue on SiO2 (EtOAc/petroleum ether, 1:4 )

Sources & evidence

ORD record: ord-552118334e3e433489f86c8ca04eda7b
Source dataset: uspto-grants-1994_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05331004

Reaction notes

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