2-Aminothiazole → 4-(2-Fluoro-6-methoxy-phenoxy)-3-nitrobenzaldehyde

HRID 2276268Notes

Reaction equation

HRID 2276268 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH3:9])[C:3]=1[OH:10].F[C:12]1[CH:19]=[CH:18][C:15]([CH:16]=[O:17])=[CH:14][C:13]=1[N+:20]([O-:22])=[O:21].C(C1C=CC(OC2C(OC)=CC=CC=2F)=C(C=1)N)=O.NC1SC=CN=1>>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH3:9])[C:3]=1[O:10][C:12]1[CH:19]=[CH:18][C:15]([CH:16]=[O:17])=[CH:14][C:13]=1[N+:20]([O-:22])=[O:21]

Participants

5

Reactant 4

HCID 21552-AminothiazoleHCID 5981294-Fluoro-3-nitrobenzaldehydeHCID 27373672-Fluoro-6-methoxyphenolHCID 865930845-Formyl-2-(2-fluoro-6-methoxy-phenoxy)-aniline2×

Product 1

HCID 865930834-(2-Fluoro-6-methoxy-phenoxy)-3-nitrobenzaldehydeYield 70%

Procedure

4-(2-Fluoro-6-methoxy-phenoxy)-3-nitrobenzaldehyde (1.0 g, 70%) was prepared from 2-fluoro-6-methoxyphenol (0.78 g, 5.5 mmol) and 4-fluoro-3-nitrobenzaldehyde (0.84 g, 5.0 mmol) following the general procedure A. This was reduced to 5-formyl-2-(2-fluoro-6-methoxy-phenoxy)-aniline (0.57 g, 62%) following general procedure B. 1-[2-(2-Fluoro-6-methoxy-phenoxy)-5-fonnyl-phenyl]-3-thiazol-2-yl-urea (265 mg, 69%) was prepared from 5-formyl-2-(2-fluoro-6-methoxy-phenoxy)-aniline (261 mg, 1.0 mmol) and 2-aminothiazole (100 mg, 1.0 mmol) following the general procedure D.

Sources & evidence

ORD record
ord-f9c0714c115f4f6db0422fbe6a7c2218
Source dataset
uspto-grants-2015_09
Patent number
USRE045670E1

Reaction notes

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