Thiourea → HCID 178476697, compound

HRID 444559Notes

Reaction equation

HRID 444559 reaction equation
[C:1]([O:4][N:5]=[C:6]([C:23](=O)[CH2:24]Br)[C:7]([O:9][CH:10]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8])(=[O:3])[CH3:2].[NH2:27][C:28]([NH2:30])=[S:29]>CN(C)C(=O)C>[C:1]([O:4][N:5]=[C:6]([C:23]1[NH:30][C:28](=[NH:27])[S:29][CH:24]=1)[C:7]([O:9][CH:10]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 2723790ThioureaHCID 54003458HCID 54003458, compound

Product 1

HCID 178476697HCID 178476697, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

In 20 ml of N,N-dimethylacetamide there were dissolved 26.5 g of benzhydryl 2-acetoxyimino-4-bromo-3-oxobutyrate and, under ice-cooling and stirring, 4.81 g of thiourea were added. The mixture was stirred at room temperature for 3 hours and 15 minutes, after which it was washed well with 80 ml of ether. The ether was discarded after being removed by decantation. The above procedure was carried out once again and the mixture was poured into 100 ml of water, whereupon crystals separated out. After loosening, the crystals were recovered by filtration and washed with ether, a small amount of ethyl acetate and ether in the order mentioned. By the above procedure there were obtained 10.738 g of crystals of the captioned compound.

Workup

  1. temperatureunder ice-cooling
  2. stirringThe mixture was stirred at room temperature for 3 hours and 15 minutes
  3. washafter which it was washed well with 80 ml of ether
  4. customafter being removed by decantation
  5. additionthe mixture was poured into 100 ml of water, whereupon crystals
  6. customseparated out
  7. filtrationthe crystals were recovered by filtration
  8. washwashed with ether

Sources & evidence

ORD record
ord-1925c9036cf74106900eeb96f01aa6d3
Source dataset
uspto-grants-1981_04
Patent number
US04264595

Reaction notes

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