3,4-Dichloroaniline → HCID 178424838, compound

HRID 2185188Notes

Reaction equation

HRID 2185188 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[N:19]=[C:18]([OH:20])[C:17]3[C:12](=[C:13](I)[CH:14]=[C:15]([F:21])[CH:16]=3)[N:11]=2)[CH:5]=[CH:6][C:7]=1[Cl:8].ClC1N=C(O)[C:31]2[C:26](=[C:27](I)[CH:28]=C(F)[CH:30]=2)N=1.ClC1C=C(C=CC=1Cl)N.CN1[CH2:51][CH2:50][CH2:49][C:48]1=O>>[CH3:48][C:49]1[CH:28]=[CH:27][C:26](/[CH:31]=[CH:30]/[C:13]2[CH:14]=[C:15]([F:21])[CH:16]=[C:17]3[C:12]=2[N:11]=[C:10]([NH:9][C:4]2[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=2)[N:19]=[C:18]3[OH:20])=[CH:51][CH:50]=1

Participants

5

Reactant 4

HCID 72573,4-DichloroanilineHCID 13387N-methyl-2-pyrrolidoneHCID 178517821HCID 178517821, compoundHCID 178518006HCID 178518006, compound

Product 1

HCID 178424838HCID 178424838, compound

Procedure

2-((3,4-Dichlorophenyl)amino)-6-fluoro-8-iodoquinazolin-4-ol. A solution of 2-chloro-6-fluoro-8-iodoquinazolin-4-ol (3.0 g) and 3,4-dichloroaniline (4.49 g) in N-methylpyrrolidone (60 mL) was heated to 120° C. for 3.5 h. After cooling to room temperature, the reaction mixture was quenched into ice/water. The precipitate which formed was isolated by filtration, washed with water and dried to afford the title compound as a light yellow solid (3.32 g). 1H NMR (300 MHz, DMSO-d6): δ11.23 (brs, 1H), 9.16 (s, 1H), 8.82 (d, J=2.1 Hz, 1H), 8.20 (dd, J=3 & 8.1 Hz, 1H), 7.72 (dd, J=3 & 8.4 Hz, 1H), 7.55 (m, 2H).

Workup

  1. customthe reaction mixture was quenched into ice/water
  2. customThe precipitate which formed
  3. customwas isolated by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-2e16f0b4682f4b1bad76c6a7338d056c
Source dataset
uspto-grants-2002_06
Patent number
US06399603B1

Reaction notes

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