Dimethylformamide → HCID 13537742, compound

HRID 1583968Notes

Reaction equation

HRID 1583968 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([O:13][CH3:14])=[N:10][S:11][N:12]=2)=[CH:4][CH:3]=1.[Cu](C#N)[C:16]#[N:17].CN(C)C=O.[C-]#N.[Na+]>O>[C:16]([C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([O:13][CH3:14])=[N:10][S:11][N:12]=2)=[CH:4][CH:3]=1)#[N:17]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8929Sodium CyanideHCID 13537740HCID 13537740, compoundHCID 178418260HCID 178418260, compound

Product 1

HCID 13537742HCID 13537742, compoundYield 62.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a manner similar to L. Friedman and H. Shechter, J. O. C., 26, 2522 (1961), incorporated herein by reference, 1.15 g (0.0043 mole) of 4-(4-bromophenyl)-3-methoxy-1,2,5-thiadiazole, 0.46 g (0.0051 mole) of copper cyanide, 15 ml of N,N-dimethylformamide, and a solution of 66.5 g of sodium cyanide in 200 ml of water were reacted to produce 0.58 g of 4-(4-cyanophenyl)-3-methoxy-1,2,5-thiadiazole, Compound 30 of Table I. Compounds 8 and 44 were also prepared by this method.

Sources & evidence

ORD record
ord-03b558c1c2ff4e05a25f223fa17c4a5a
Source dataset
uspto-grants-1985_11
Patent number
US04555521

Reaction notes

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