Benzoyl isothiocyanate → 1-Benzoyl-3-(5-bromo-3-(4-fluorophenoxy)pyridin-2-yl)thiourea

HRID 911807Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]([O:9][C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)[C:5]([NH2:8])=[N:6][CH:7]=1.[C:17]([N:25]=[C:26]=[S:27])(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>>[C:17]([NH:25][C:26]([NH:8][C:5]1[C:4]([O:9][C:10]2[CH:11]=[CH:12][C:13]([F:16])=[CH:14][CH:15]=2)=[CH:3][C:2]([Br:1])=[CH:7][N:6]=1)=[S:27])(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

Reactant 2

HCID 68284Benzoyl isothiocyanate

HCID 669944905-Bromo-3-(4-fluorophenoxy)pyridin-2-amine

Product 1

HCID 866314841-Benzoyl-3-(5-bromo-3-(4-fluorophenoxy)pyridin-2-yl)thioureaYield 91.2%

Procedure

Following the procedure in Example 7, Step C, 5-bromo-3-(4-fluorophenoxy)pyridin-2-amine (800 mg, 2.83 mmol) and benzoyl isothiocyanate (0.457 mL, 3.39 mmol) afforded 1-benzoyl-3-(5-bromo-3-(4-fluorophenoxy)pyridin-2-yl)thiourea (1150 mg, 91.2% yield).

Sources & evidence

ORD record: ord-b75529ee70944a87a2f6c053fc28f955
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08022223B2

Reaction notes

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