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4-Bromo-2-fluoroaniline → N-(4-bromo-2-fluorophenyl)-6-fluoro-1,3-benzothiazol-2-amine

HRID 9586
Notes
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Reaction equation

HRID 9586 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[S:10][C:11]3[CH:17]=[CH:16][CH:15]=[C:14](C)[C:12]=3[N:13]=2)=[C:4]([F:19])[CH:3]=1.BrC1C=CC(NC2SC3C=C(OC(F)(F)[F:39])C=CC=3N=2)=C(F)C=1.ClC1SC2C=C(F)C=CC=2N=1.FC1C=C(Br)C=CC=1N>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[S:10][C:11]3[CH:17]=[C:16]([F:39])[CH:15]=[CH:14][C:12]=3[N:13]=2)=[C:4]([F:19])[CH:3]=1
ParticipantsProcedureSources & evidenceReaction notes

Participants

5

Reactant 4

HCID 1230504-Bromo-2-fluoroanilineHCID 20498702-Chloro-6-fluorobenzothiazoleHCID 21985778N-(4-bromo-2-fluorophenyl)-N-(6-trifluoromethoxy-1,3-benzothiazol-2-yl)amineHCID 23549342N-(4-bromo-2-fluorophenyl)-4-methyl-1,3-benzothiazol-2-amine

Product 1

HCID 7147089N-(4-bromo-2-fluorophenyl)-6-fluoro-1,3-benzothiazol-2-amineYield 78%

Procedure

In a similar manner to that described above for the preparation of N-(4-bromo-2-fluorophenyl)-4-methyl-1,3-benzothiazol-2-amine and N-(4-bromo-2-fluorophenyl)-N-(6-trifluoromethoxy-1,3-benzothiazol-2-yl)amine, using 2-chloro-6-fluoro-1,3-benzothiazole and 2-fluoro-4-bromoaniline, was prepared the desired product as a white solid (78% yield). 1H NMR (400 MHz, DMSO-d6) δ 10.50 (s, 1H), 8.60 (t, 1H), 7.80 (d, 1H), 7.60 (m, 2H), 7.40 (d, 1H), 7.20 (m, 1H).

Sources & evidence

ORD record
ord-3ef69b9d21794e6c8556094586f591f4
Source dataset
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07091228B2

Reaction notes

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On this pageParticipantsProcedureSources & evidenceReaction notes