4-Chlorobenzohydrazide → HCID 59536829, compound

HRID 709119Notes

Reaction equation

HRID 709119 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 initially charged at 50° C., and a solution of 10.0 g (77.5 mmol) of ethyl 2-isocyanatoacetate in 100 ml of dry THF was added dropwise. Initially, a solution was formed, and then a precipitate. After the addition had ended, the mixture was stirred at 50° C. for a further 2 h and then allowed to stand at RT overnight. The crystals were isolated by filtration, washed with a little diethyl ether and dried under high vacuum. This gave 21.43 g (89% of theory) of the title compound.

Workup

  1. additionwas initially charged at 50° C.
  2. customInitially, a solution was formed
  3. additionAfter the addition
  4. waitto stand at RT overnight
  5. customThe crystals were isolated by filtration
  6. washwashed with a little diethyl ether
  7. customdried under high vacuum

Sources & evidence

ORD record
ord-7f58fe4b59e4497996e582cce58afd88
Source dataset
uspto-grants-2015_11
Patent number
US09180120B2

Reaction notes

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