4-Chlorobenzohydrazide → HCID 59536829, compound

HRID 220627Notes

Reaction equation

HRID 220627 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-f879b56f33de4c5f86c3b42e259116eb
Source dataset
uspto-grants-2012_06
Patent number
US08202895B2

Reaction notes

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