Formaldehyde → HCID 21488688, compound

HRID 1974046Notes

Reaction equation

HRID 1974046 reaction equation
[C:1]1([N:7]2[C:11](=[O:12])[CH2:10][C:9]([NH:13][C:14](=[O:36])[CH:15]([S:32]([OH:35])(=[O:34])=[O:33])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:37]([O-])(=O)C.[NH4+].C=O.[H][H]>[Ni].C(O)C>[C:1]1([N:7]2[C:11](=[O:12])[CH:10]([CH3:37])[C:9]([NH:13][C:14](=[O:36])[CH:15]([S:32]([OH:35])(=[O:34])=[O:33])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])=[N:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 712Formaldehyde2×HCID 517165Ammonium AcetateHCID 21488689HCID 21488689, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 21488688HCID 21488688, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Conditions

Temperature
75 °C

Procedure

An autoclave was charged with 52.1 g (0.1 mole) of 1-phenyl-3-(α-sulphostearoylamino)-2-pyrazolin-5-one, 15.4 g (0.2 mole) of ammonium acetate, 4.5 g (0.15 mole) of paraformaldehyde, 10 g of Raney nickel and 535 ml of ethanol. The mixture was heated to 75° C whereupon hydrogenation started at a hydrogen pressure of 700 psi. After 30 min the hydrogen pressure was released and another 4.5 g of paraformaldehyde were added whereupon hydrogenation was continued. After having filtered off the catalyst, the filtrate was acidified with 100 ml of concentrated hydrochloric acid. The precipitate was filtered off. Yield: 41 g (75%). Melting point: 240° C.

Workup

  1. filtrationAfter having filtered off the catalyst
  2. filtrationThe precipitate was filtered off

Sources & evidence

ORD record
ord-194453e4d9754ad2a93f27c86f8092f3
Source dataset
uspto-grants-1976_12
Patent number
US04000156

Reaction notes

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