Phosphorus pentachloride → 2-Dimethylamino-4-methyl-thiazole-5-carboxylic acid (cyano-thiophen-2-yl-methyl)-amide

HRID 439288Notes

Reaction equation

HRID 439288 reaction equation
[CH3:1][N:2]([CH3:12])[C:3]1[S:4][C:5]([C:9]([OH:11])=O)=[C:6]([CH3:8])[N:7]=1.CN(C)C1SC(C(Cl)=O)=C(C)N=1.P(Cl)(Cl)(Cl)(Cl)Cl.Cl.[NH2:32][CH:33]([C:36]1[S:37][CH:38]=[CH:39][CH:40]=1)[C:34]#[N:35]>C(N(CC)CC)C>[C:34]([CH:33]([NH:32][C:9]([C:5]1[S:4][C:3]([N:2]([CH3:1])[CH3:12])=[N:7][C:6]=1[CH3:8])=[O:11])[C:36]1[S:37][CH:38]=[CH:39][CH:40]=1)#[N:35]

Participants

6

Reactant 4

HCID 24819Phosphorus pentachlorideHCID 133524562-Thiopheneacetonitrile, a-amino-, monohydrochlorideHCID 235097472-(Dimethylamino)-4-methyl-1,3-thiazole-5-carboxylic acidHCID 450818742-(Dimethylamino)-4-methyl-1,3-thiazole-5-carbonyl chloride

Product 1

HCID 536401912-Dimethylamino-4-methyl-thiazole-5-carboxylic acid (cyano-thiophen-2-yl-methyl)-amideYield 36%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

1.2g of 2-dimethylamino-4-methyl-thiazole-5-carboxylic acid was converted into 2-dimethylamino-4-methyl-thiazole-5-carboxylic acid chloride using 1.3g of phosphorus pentachloride according to the same procedure as EXAMPLE 1. Then 1.1g of amino-thiophen-2-yl-acetonitrile hydrochloride and 2.5ml of triethylamine were added thereto and the reaction mixture was treated according to the same procedure as EXAMPLE 1 to obtain 0.65g (Yield 36%) of the title compound.

Workup

  1. additionthe reaction mixture was treated

Sources & evidence

ORD record
ord-24a62718899f49e6b83846e1bfde1c01
Source dataset
uspto-grants-1996_05
Patent number
US05514643

Reaction notes

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