4-Chlorobenzohydrazide → HCID 59536829, compound

HRID 536538Notes

Reaction equation

HRID 536538 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-chlorobenzohydrazide 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 and then left to stand overnight at RT. The crystals were isolated by filtration, washed with a little diethyl ether and dried in a high vacuum. 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 a high vacuum

Sources & evidence

ORD record
ord-5f95c2cdd37549fc8638e2d8870737b6
Source dataset
uspto-grants-2014_10
Patent number
US08859601B2

Reaction notes

Loading…