Benzyl isocyanate → HCID 10287046, compound

HRID 583794Notes

Reaction equation

HRID 583794 reaction equation
[CH2:1]([O:8][C:9]([C:11]1[S:12][C:13]([NH2:16])=[N:14][N:15]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:17]([N:24]=[C:25]=[O:26])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C1COCC1>[CH2:1]([O:8][C:9]([C:11]1[S:12][C:13]([NH:16][C:25]([NH:24][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:26])=[N:14][N:15]=1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 76639Benzyl isocyanateHCID 69693505HCID 69693505, compound

Product 1

HCID 10287046HCID 10287046, compoundYield 76.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the product of Step (d) (0.1 g, 0.000425 mol) in THF (6.07 mL) was added benzyl isocyanate (0.0525 mL, 0.000425 mol), and the mixture was stirred overnight at room temperature. After 24 hours, the mixture was rotary evaporated and the concentrate was diluted with ethyl ether and dichloromethane. A solid was filtered and washed with ethyl ether. The mother filtrate was rotary evaporated and the residue triturated with ethyl ether and dichloromethane to give additional solids. The solids were combined to give 0.12 g of 5-(3-benzyl-ureido)-1,3,4-thiadiazole-2-carboxylic acid benzyl ester; mp 188-192° C.

Workup

  1. waitAfter 24 hours
  2. customthe mixture was rotary evaporated
  3. additionthe concentrate was diluted with ethyl ether and dichloromethane
  4. filtrationA solid was filtered
  5. washwashed with ethyl ether
  6. customThe mother filtrate was rotary evaporated
  7. customthe residue triturated with ethyl ether and dichloromethane
  8. customto give additional solids

Sources & evidence

ORD record
ord-2c226992af00484baa754a37a96fb9a0
Source dataset
uspto-grants-2005_08
Patent number
US06924276B2

Reaction notes

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