Bromomethyl isobutyrate → HCID 178419598, compound

HRID 59856Notes

Reaction equation

HRID 59856 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[NH:10][C:11]([NH2:13])=[S:12].[C:14]([O:19][CH2:20][Br:21])(=[O:18])[CH:15]([CH3:17])[CH3:16]>CC(C)=O>[BrH:21].[C:14]([O:19][CH2:20][S:12]/[C:11](=[N:10]/[C:3]1[CH:4]=[CH:5][C:6]([O:8][CH3:9])=[CH:7][C:2]=1[CH3:1])/[NH2:13])(=[O:18])[CH:15]([CH3:17])[CH3:16]

Participants

4

Reactant 2

HCID 20156133Bromomethyl isobutyrateHCID 20481024(4-Methoxy-2-methylphenyl)thiourea

Product 1

HCID 178419598HCID 178419598, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
0 °C

Procedure

2-Methyl-4-methoxyphenyl thiourea (0.5 grams (g), 2.55 millimoles (mmol)) and bromomethyl isobutyrate were combined in 5 mL of acetone at ambient temperature, and the solution was allowed to stir for 18 hours (h). The solution was then cooled to 0° C. and the resulting solid was filtered and air-dried to give (E)-(N′-(4-methoxy-2-methylphenyl)carbamimidoylthio)methyl isobutyrate HBr (B1) (0.83 g, 82%): mp 127-130° C.; 1H NMR (CDCl3) δ 11.34 (s, 1H), 10.29 (s, 1H), 8.32 (s, 1H), 7.09 (d, J=8.7 Hz, 1H), 6.79 (d, J=2.8 Hz, 1H), 6.74 (dd, J=8.7, 2.8 Hz, 1H), 3.81 (s, 3H), 2.69 (heptet, J=7.0 Hz, 1H), 2.31 (s, 3H), 1.22 (d, J=7.0 Hz, 6H); ESIMS m/z 297 ([M+H]+).

Workup

  1. filtrationthe resulting solid was filtered
  2. customair-dried

Sources & evidence

ORD record
ord-e8db3d1d127940739043a3baf25f60d0
Source dataset
uspto-grants-2016_09
Patent number
US09440964B2

Reaction notes

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