Bromide ion → Pseudourea, 2-(p-nitrobenzyl)-2-thio-, monohydrobromide

HRID 1513325Notes

Reaction equation

HRID 1513325 reaction equation
[NH2:1][C:2]([NH2:4])=[S:3].[N+:5]([C:8]1[CH:13]=[CH:12][C:11]([CH2:14][Br:15])=[CH:10][CH:9]=1)([O-:7])=[O:6].[Br-]>CC(C)=O>[BrH:15].[N+:5]([C:8]1[CH:13]=[CH:12][C:11]([CH2:14][S:3][C:2](=[NH:4])[NH2:1])=[CH:10][CH:9]=1)([O-:7])=[O:6]

Participants

5

Reactant 3

HCID 259Bromide ion2×HCID 660114-Nitrobenzyl bromideHCID 2723790Thiourea2×

Product 1

HCID 116350Pseudourea, 2-(p-nitrobenzyl)-2-thio-, monohydrobromideYield 94.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

Thiourea (8c) (1.55 kg) and acetone (30 L) were added to a 72-L reactor under a nitrogen atmosphere. The mixture was agitated. 4-nitrophenylmethyl bromide (8d) (4.00 kg) and acetone (15 L) were added to a separate flask. The mixture was stirred until the bromide dissolved (warming may be required). The solution of the bromide was added to the mixture of thiourea, keeping the temperature below 40° C. A thick solution formed within 30 minutes. After stiffing for 2 h, HPLC analysis of the mixture shows >99% conversion. The mixture was filtered, and the filter cake was rinsed with a 1:1 MTBE: acetone solution (8 L). The solids were dried to give 5.09 kg (93% yield) of the desired product (8a) as a white solid.

Workup

  1. dissolutiondissolved
  2. temperature(warming may be required)
  3. customthe temperature below 40° C
  4. customA thick solution formed within 30 minutes
  5. filtrationThe mixture was filtered
  6. washthe filter cake was rinsed with a 1:1 MTBE
  7. customThe solids were dried

Sources & evidence

ORD record
ord-a2ddd57e1f59443f9dfb1d9db5f8f946
Source dataset
uspto-grants-2012_07
Patent number
US08217172B2

Reaction notes

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