Allyl bromide → HCID 178460856, compound

HRID 1733366Notes

Reaction equation

HRID 1733366 reaction equation
[NH:1]=[C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:9][CH2:10][CH3:11])=[C:4]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:3]1[NH:19][C:20]([NH:22][C:23]([O:25][CH3:26])=[O:24])=[S:21].[OH-].[Na+].[CH2:29](Br)[CH:30]=[CH2:31]>CC(C)=O.O>[NH:1]=[C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:9][CH2:10][CH3:11])=[C:4]([CH2:12][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:3]1[NH:19][C:20](=[N:22][C:23]([O:25][CH3:26])=[O:24])[S:21][CH2:31][CH:30]=[CH2:29]

Participants

6

Reactant 3

HCID 7841Allyl bromideHCID 14798Sodium Hydroxide2×HCID 131711976HCID 131711976, compound

Product 1

HCID 178460856HCID 178460856, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent2×

Procedure

To a suspension of 1-iminophenylmethyl-2-(3-carbomethoxythioureido)-4-propylthiobenzene (1.0 g.) in acetone (30 ml.) and water (10 ml.) there is added aqueous sodium hydroxide (0.21 g.). The mixture is stirred at room temperature for one hour (a solution forms 20 minutes after the addition of sodium hydroxide) and to it there is added allyl bromide (0.36 g.). The solution is stirred at room temperature for two hours and is then poured into water (300 ml.). The mixture is stirred at room temperature for 24 hours and is vacuum filtered. The tacky yellow solid is stirred in hexane (50 ml.) and is filtered to yield 0.35 g. of 1-iminohexylmethyl-2-(3-carbomethoxy-S-isothioureido)-4-propylthiobenzene, m.p. 70°-72° C.

Workup

  1. stirringThe solution is stirred at room temperature for two hours
  2. stirringThe mixture is stirred at room temperature for 24 hours
  3. filtrationfiltered
  4. stirringThe tacky yellow solid is stirred in hexane (50 ml.)
  5. filtrationis filtered
  6. customto yield 0.35 g

Sources & evidence

ORD record
ord-906bdb8ecd384d859145044b2e6230f5
Source dataset
uspto-grants-1980_12
Patent number
US04241079

Reaction notes

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