Benzoyl isothiocyanate → 1-Benzoyl-3-(4-(benzyloxy)-5-bromopyridin-2-yl)thiourea

HRID 911062Notes

Reaction equation

HRID 911062 reaction equation
[CH2:1]([O:8][C:9]1[C:14]([Br:15])=[CH:13][N:12]=[C:11]([NH2:16])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=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>C1COCC1>[C:17]([NH:25][C:26]([NH:16][C:11]1[CH:10]=[C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:14]([Br:15])=[CH:13][N:12]=1)=[S:27])(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 68284Benzoyl isothiocyanateHCID 66618159HCID 66618159, compound

Product 1

HCID 866347751-Benzoyl-3-(4-(benzyloxy)-5-bromopyridin-2-yl)thioureaYield 91.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A flask was charged with 4-(benzyloxy)-5-bromopyridin-2-amine (6.90 g, 24.7 mmol), and THF (250 mL). Benzoyl isothiocyanate (4.24 g, 26.0 mmol) was added and the reaction was stirred at ambient temperature overnight. The reaction mixture was concentrated, and 9:1 Hexanes:ethyl acetate (400 mL) was added to the residue. The suspension was filtered to give the desired product (10 g, 82.3% yield) as light brown solid.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. addition9:1 Hexanes:ethyl acetate (400 mL) was added to the residue
  3. filtrationThe suspension was filtered

Sources & evidence

ORD record
ord-baede6bb2c7b4824a17ca99cfc25060e
Source dataset
uspto-grants-2011_09
Patent number
US08022222B2

Reaction notes

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