Thiophosgene → 4-(3-Chloro-4-fluoroanilino)-6-isothiocyanato-7-methoxyquinazoline

HRID 618679Notes

Reaction equation

HRID 618679 reaction equation
[C:1](Cl)(Cl)=[S:2].[NH2:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][C:15]=1[O:16][CH3:17])[N:12]=[CH:11][N:10]=[C:9]2[NH:18][C:19]1[CH:24]=[CH:23][C:22]([F:25])=[C:21]([Cl:26])[CH:20]=1>Cl>[Cl:26][C:21]1[CH:20]=[C:19]([CH:24]=[CH:23][C:22]=1[F:25])[NH:18][C:9]1[C:8]2[C:13](=[CH:14][C:15]([O:16][CH3:17])=[C:6]([N:5]=[C:1]=[S:2])[CH:7]=2)[N:12]=[CH:11][N:10]=1

Participants

4

Reactant 2

HCID 10040ThiophosgeneHCID 21847826N4-(3-Chloro-4-fluorophenyl)-7-methoxy-4,6-quinazolinediamine

Product 1

HCID 218478394-(3-Chloro-4-fluoroanilino)-6-isothiocyanato-7-methoxyquinazoline

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

After repetition of the previous steps, thiophosgene (0.5 ml) was added dropwise to a stirred solution of 6-amino4-(3-chloro-4-fluoroanilino)-7-methoxyquinazoline (1.65 g) in 2N aqueous hydrochloric acid (45 ml). The mixture was stirred at ambient temperature for 16 hours. The precipitate was isolated and dried to give 4-(3-chloro-4-fluoroanilino)-6-isothiocyanato-7-methoxyquinazoline which was used without further purification.

Workup

  1. customThe precipitate was isolated
  2. customdried

Sources & evidence

ORD record
ord-f5e3aaaa7703448aa3a8e47b38958f2d
Source dataset
uspto-grants-1999_09
Patent number
US05955464

Reaction notes

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