Acetylthiourea → HCID 13922713, compound

HRID 2166021Notes

Reaction equation

HRID 2166021 reaction equation
Cl[CH2:2][C:3](=O)[C:4](=[CH:12][CH3:13])[C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6].[C:15]([NH:18][C:19]([NH2:21])=[S:20])(=[O:17])[CH3:16]>CN(C)C=O.O>[C:15]([NH:18][C:19]1[S:20][CH:2]=[C:3](/[C:4](=[CH:12]/[CH3:13])/[C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6])[N:21]=1)(=[O:17])[CH3:16]

Participants

5

Reactant 2

HCID 2723593AcetylthioureaHCID 56621722HCID 56621722, compound

Product 1

HCID 13922713HCID 13922713, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
85 °C

Procedure

The crude product of a 2.2 mol batch of tert.-butyl 4-chloro-2-ethylidene-3-oxobutyrate, dissolved in 100 ml of dimethylformamide, is added to a solution, warmed to 85° C., of 236 g (2 mol) of acetylthiourea in a mixture of 360 ml of water and 720 ml of dimethylformamide. The mixture is stirred at 85° C. for two hours and concentrated, the residue is taken up in ethyl acetate and the solution is extracted three times with water. After drying and concentrating, by-products are precipitated with ether.

Workup

  1. additionis added to a solution
  2. concentrationconcentrated
  3. extractionthe solution is extracted three times with water
  4. customAfter drying
  5. concentrationconcentrating
  6. customby-products are precipitated with ether

Sources & evidence

ORD record
ord-ca8b2659d9b044169380de4e9f2679c3
Source dataset
uspto-grants-1990_07
Patent number
US04943568

Reaction notes

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