Chloroacetyl chloride → N'-(2-chloroacetyl)-3-cyanobenzohydrazide

HRID 732128Notes

Reaction equation

HRID 732128 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][CH:12]=1)[C:6]([NH:8][NH2:9])=[O:7])#[N:2].C1COCC1.[Cl:18][CH2:19][C:20](Cl)=[O:21]>CN(C=O)C>[Cl:18][CH2:19][C:20]([NH:9][NH:8][C:6](=[O:7])[C:5]1[CH:10]=[CH:11][CH:12]=[C:3]([C:1]#[N:2])[CH:4]=1)=[O:21]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8028TetrahydrofuranHCID 219426583-Cyanobenzohydrazide

Product 1

HCID 54595588N'-(2-chloroacetyl)-3-cyanobenzohydrazideYield 69%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

3-cyanobenzohydrazide (1.6 g, 10.0 mmol) was added to THF (40 ml) and DMF (10 ml). TEA (1.4 ml, 10.0 mmol) was added at 0° C. followed by chloroacetyl chloride (1.0 ml, 12.6 mmol) and the reaction mixture was stirred at 0° C. for 1 h and at rt for 2 h. The THF was evaporated, water was added to the remaining mixture, followed by filtratation over celite and purification with prep. HPLC to give the title compound (1.6 g, 69%). 1H NMR (DMSO-d6): 10.62 (br s, 2 H), 8.28 (m, 1 H), 8.18 (m, 1 H), 8.08 (m, 1 H), 7.75 (t, 1 H), 4.22 (s, 2 H).

Workup

  1. customThe THF was evaporated
  2. additionwater was added to the remaining mixture
  3. customfollowed by filtratation over celite and purification with prep

Sources & evidence

ORD record
ord-d846238eb2fb48888bece67cafb46889
Source dataset
uspto-grants-2009_09
Patent number
US07585881B2

Reaction notes

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