3,4-Dichloroaniline → HCID 178526503, compound

HRID 2185189Notes

Reaction equation

HRID 2185189 reaction equation
Cl[C:2]1[N:11]=[C:10]([OH:12])[C:9]2[C:4](=[C:5]([CH:16]3[O:20][CH2:19][CH2:18][O:17]3)[CH:6]=[C:7]([N+:13]([O-:15])=[O:14])[CH:8]=2)[N:3]=1.[Cl:21][C:22]1[CH:23]=[C:24]([CH:26]=[CH:27][C:28]=1[Cl:29])[NH2:25].C(N(CC)C(C)C)(C)C>CN(C)C(=O)C.O>[Cl:21][C:22]1[CH:23]=[C:24]([NH:25][C:2]2[N:11]=[C:10]([OH:12])[C:9]3[C:4](=[C:5]([CH:16]4[O:20][CH2:19][CH2:18][O:17]4)[CH:6]=[C:7]([N+:13]([O-:15])=[O:14])[CH:8]=3)[N:3]=2)[CH:26]=[CH:27][C:28]=1[Cl:29]

Participants

6

Reactant 3

HCID 72573,4-DichloroanilineHCID 81531DiisopropylethylamineHCID 178526502HCID 178526502, compound

Product 1

HCID 178526503HCID 178526503, compoundYield 63.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 31374DimethylacetamideSolvent

Procedure

A solution of 2-chloro-8-(1,3-dioxolan-2-yl)-4-hydroxy-6-nitroquinazoline (2.9 g), 3,4-dichloroaniline (3.2 g) and N,N-diisopropylethylamine (2.52 mL) in N,N-dimethylacetamide (145 mL) was heated to 140° C. for 3.3 hours. The mixture was then cooled to room temperature and diluted with water (2 L). The aqueous solution was separated into two equal portions, and each portion was extracted with ethyl acetate (7×100 mL). The combined ethyl acetate extracts were washed with 2N hydrochloric acid until all of the excess 3,4-dichloroaniline was removed, dried over Na2SO4, filtered and evaporated to afford the title compound as a brown solid (2.6 g). 1H NMR (300 MHz, DMSO-d6): 8.67 (d, J=2.7 Hz, 1H), 8.48 (d, J=2.7 Hz, 1H), 8.45 (d, J=2.7 Hz, 1H), 7.58 (d, J=8.7 Hz, 1H), 7.42 (dd, J=2.7, 8.7 Hz, 1H), 6.23 (s, 1H), 4.09 (m, 4H). HPLC Method A: 7.76 min.

Workup

  1. customThe aqueous solution was separated into two equal portions
  2. extractioneach portion was extracted with ethyl acetate (7×100 mL)
  3. washThe combined ethyl acetate extracts were washed with 2N hydrochloric acid until all of the excess 3,4-dichloroaniline
  4. customwas removed
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-77b0bb516e1e4d749277c67bdc680b82
Source dataset
uspto-grants-2002_06
Patent number
US06399603B1

Reaction notes

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