3-Bromoaniline → HCID 5328418, compound

HRID 394759Notes

Reaction equation

Cl[C:2]1[C:7]2[S:8][C:9]3[C:14]([N+:15]([O-:17])=[O:16])=[CH:13][CH:12]=[CH:11][C:10]=3[C:6]=2[N:5]=[CH:4][N:3]=1.[Br:18][C:19]1[CH:20]=[C:21]([CH:23]=[CH:24][CH:25]=1)[NH2:22].Cl.BrC1C=C(C=CC=1)N>C(O)(C)C>[Br:18][C:19]1[CH:20]=[C:21]([NH:22][C:2]2[C:7]3[S:8][C:9]4[C:14]([N+:15]([O-:17])=[O:16])=[CH:13][CH:12]=[CH:11][C:10]=4[C:6]=3[N:5]=[CH:4][N:3]=2)[CH:23]=[CH:24][CH:25]=1

Participants

Conditions

Temperature: 85 °C

Procedure

A mixture of 4-chloro-6-nitrobenzothienopyrimidine (166 mg, 0.62 mmol), m-bromoaniline (0.08 mL, 0.73 mmol) and m-bromoaniline hydrochloride (144 mg, 0.69 mmol) in isopropanol (4.5 mL) was heated at 85° C. stirring under N2 for 7.5 hours. The dark brown solid was collected by Buchner filtration and washed with isopropanol and air dried to give 4-([3-bromophenyl]amino)-6-nitrobenzothieno[3,2-d]pyrimidine (145 mg, 67%), mp 247.0-248.1° C.

Workup

filtrationThe dark brown solid was collected by Buchner filtration
washwashed with isopropanol and air
customdried

Sources & evidence

ORD record: ord-1b3ccfaf5b834b76ad72b25503d22862
Source dataset: uspto-grants-2003_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06602863B1

Reaction notes

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