2,4-Dichloro-5-fluoroaniline → HCID 178505942, compound

HRID 70950Notes

Reaction equation

HRID 70950 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([Cl:11])[C:5]2[NH:6][N:7]=[N:8][C:4]=2[C:3]=1[F:12].[Cl:13][C:14]1[CH:20]=[C:19]([Cl:21])[C:17]([NH2:18])=[C:16]([N+:22]([O-:24])=[O:23])[C:15]=1[F:25].Cl[C:27]1C=C(Cl)C(F)=CC=1N>>[NH2:18][C:17]([CH3:27])([CH2:19][N:7]1[N:6]=[C:5]2[C:9]([Cl:11])=[CH:10][C:2]([Cl:1])=[C:3]([F:12])[C:4]2=[N:8]1)[C:16]#[N:22].[Cl:1][C:2]1[CH:10]=[C:9]([Cl:11])[C:5]2[NH:6][N:7]=[N:8][C:4]=2[C:3]=1[F:12].[Cl:13][C:14]1[CH:20]=[C:19]([Cl:21])[C:17]([NH2:18])=[C:16]([N+:22]([O-:24])=[O:23])[C:15]=1[F:25]

Participants

6

Reactant 3

HCID 27580982,4-Dichloro-5-fluoroanilineHCID 86625563HCID 86625563, compoundHCID 178505942HCID 178505942, compound

Product 3

HCID 666199272-Amino-3-(5,7-dichloro-4-fluoro-2H-benzotriazol-2-yl)-2-methylpropionitrileHCID 86625563HCID 86625563, compoundHCID 178505942HCID 178505942, compoundYield 85%

Procedure

2-Amino-3-(5,7-dichloro-4-fluoro-2H-benzotriazol-2-yl)-2-methylpropionitrile [1.3 g, Rf=0.2 (1:1 EA/heptane)] was prepared using a procedure similar to that described in Example 1, part a and b, except starting from 5,7-dichloro-4-fluoro-1H-benzotriazole. 5,7-Dichloro-4-fluoro-1H-benzotriazole (4 g, 85%) was prepared using a procedure similar to that described in Example 11, part a, except starting from 4,6-dichloro-3-fluoro-2-nitroaniline. 4,6-Dichloro-3-fluoro-2-nitroaniline (6.1 g) was prepared using a procedure similar to that described in Example 39, part a, b and c, except starting from 2,4-dichloro-5-fluoroaniline (10 g).

Sources & evidence

ORD record
ord-ccb8d538cfbb48bca04ab858b6078fd8
Source dataset
uspto-grants-2014_09
Patent number
US08822689B2

Reaction notes

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