Thiourea → HCID 766578, compound

HRID 1948338Notes

Reaction equation

HRID 1948338 reaction equation
Br[CH:2]([CH3:10])[C:3](=O)[C:4]([O:6][CH2:7][CH3:8])=[O:5].[NH2:11][C:12]([NH2:14])=[S:13]>>[NH2:14][C:12]1[S:13][C:2]([CH3:10])=[C:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])[N:11]=1

Participants

3

Reactant 2

HCID 2723790ThioureaHCID 11117285Ethyl 3-bromo-2-oxobutanoate2×

Product 1

HCID 766578HCID 766578, compoundYield 55%

Procedure

Ethyl 3-bromo-2-oxobutanoate (Intermediate 177, 12.2 g; 58.7 mmol) and thiourea (4.46 g; 76.1; 58.7 mmol) were combined and heated to reflux. The solution was allowed to cool to room temperature and stir for 12 hours. The reaction was monitored by LC/MS. The base was precipitated with 20% NH4OH (10 ml) and then redissolved with 1N HCl (100 ml) and then finally reprecipitated with 20% NH4OH. The precipitate was collected and washed with H2O. The crude product was then crystallized from 9:1 ethanol/water to give 5.95 g of product in 55% yield. MS (ES) MH+: 187 for C7H10N2O2S.

Workup

  1. temperatureheated to reflux
  2. customThe base was precipitated with 20% NH4OH (10 ml)
  3. dissolutionredissolved with 1N HCl (100 ml)
  4. customfinally reprecipitated with 20% NH4OH
  5. customThe precipitate was collected
  6. washwashed with H2O
  7. customThe crude product was then crystallized from 9:1 ethanol/water

Sources & evidence

ORD record
ord-972529d118914ca2a5de7ab38c1c6e84
Source dataset
uspto-grants-2013_03
Patent number
US08399489B2

Reaction notes

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