Ammonium thiocyanate → HCID 13768634, compound

HRID 2290559Notes

Reaction equation

HRID 2290559 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].[S-:11][C:12]#[N:13].[NH4+].[CH3:15][C:16]1[CH:17]=[C:18]([CH:20]=[CH:21][C:22]=1[N:23]1[CH:27]=[CH:26][CH:25]=[CH:24]1)[NH2:19]>CC(C)=O>[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([NH:13][C:12]([NH:19][C:18]1[CH:20]=[CH:21][C:22]([N:23]2[CH:27]=[CH:26][CH:25]=[CH:24]2)=[C:16]([CH3:15])[CH:17]=1)=[S:11])=[O:5]

Participants

5

Reactant 3

HCID 15666Ammonium thiocyanateHCID 691102-Chlorobenzoyl chlorideHCID 64846963-Methyl-4-(1H-pyrrol-1-yl)benzenamine

Product 1

HCID 13768634HCID 13768634, compoundYield 95.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

In a manner similar to Douglas and Dains, J. Am. Chem. Soc., 56, 719 (1934), the reaction of 3.1 g (0.017 mole) of 2-chlorobenzoyl chloride with 1.3 g (0.017 mole) of ammonium thiocyanate and 3.0 g (0.017 mole) of 3-methyl-4-(1H-pyrrol-1-yl)aniline (compound of Example 2) in 100 ml of acetone produced 6.0 g of 2-chloro-N-[[[3-methyl-4-(1H-pyrrol-1-yl)phenyl]amino]thioxomethyl]benzamide (mp 134°-136° C.).

Sources & evidence

ORD record
ord-55a3b57f5a374298bf0178d35e66b293
Source dataset
uspto-grants-1986_10
Patent number
US04617316

Reaction notes

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