4-Chlorobenzohydrazide → HCID 59536829, compound

HRID 2402763Notes

Reaction equation

HRID 2402763 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([NH:8][NH2:9])=[O:7])=[CH:4][CH:3]=1.[N:12]([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[C:13]=[O:14]>C1COCC1>[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([NH:8][NH:9][C:13]([NH:12][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[O:14])=[O:7])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 108164-ChlorobenzohydrazideHCID 76283Ethyl isocyanatoacetate

Product 1

HCID 59536829HCID 59536829, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
50 °C

Procedure

A suspension of 12.95 g (75.9 mmol) of 4-chlorobenzhydrazide in 50 ml of dry THF was introduced at 50° C. and admixed dropwise with a solution of 10.0 g (77.5 mmol) of ethyl 2-isocyanatoacetate in 100 ml of dry THF. First of all a solution formed, and then a precipitate was produced. After the end of the addition, the mixture was stirred at 50° C. for 2 h more, then left to stand overnight at RT. The crystals were isolated by filtration, washed with a little diethyl ether and dried in an HV. This gave 21.43 g (89% of theory) of the title compound.

Workup

  1. additionwas introduced at 50° C.
  2. customFirst of all a solution formed
  3. customa precipitate was produced
  4. additionAfter the end of the addition
  5. waitleft
  6. waitto stand overnight at RT
  7. customThe crystals were isolated by filtration
  8. washwashed with a little diethyl ether
  9. customdried in an HV

Sources & evidence

ORD record
ord-2af523dd050d4b76aa854521768d5791
Source dataset
uspto-grants-2014_08
Patent number
US08796324B2

Reaction notes

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