Ethanol → HCID 53873377, compound

HRID 1732301Notes

Reaction equation

[NH2:1][C:2]1[S:3][C:4]([C:7]2[CH:12]=[C:11]([O:13][CH3:14])[C:10]([O:15][CH3:16])=[C:9]([O:17][CH3:18])[CH:8]=2)=[N:5][N:6]=1.[CH3:19][O:20][C:21]([C:23]#[C:24][C:25]([O:27]C)=O)=[O:22].[CH2:29](O)C>>[CH2:19]([O:20][C:21]([C:23]1[N:6]2[N:5]=[C:4]([C:7]3[CH:8]=[C:9]([O:17][CH3:18])[C:10]([O:15][CH3:16])=[C:11]([O:13][CH3:14])[CH:12]=3)[S:3][C:2]2=[N:1][C:25](=[O:27])[CH:24]=1)=[O:22])[CH3:29]

Participants

Reactant 3

HCID 702Ethanol

HCID 12980Dimethyl acetylenedicarboxylate

HCID 2142751,3,4-Thiadiazol-2-amine, 5-(3,4,5-trimethoxyphenyl)-

Product 1

HCID 53873377HCID 53873377, compound

Procedure

The reaction of 9.7 g of 2-amino-5-(3', 4', 5'-trimethoxyphenyl)-1,3,4-thiadiazole with 6.2 g of acetylene dicarboxylic acid dimethyl ester in 200 ml of ethanol in accordance with Example 12 gives 2-(3',4',5'-trimethoxyphenyl)-7H-1,3,4-thiadiazolo-[3,2-a]-pyrimidin-7-one-5-carboxylic acid ethyl ester which, as a crude product, melts at 205°-207° C. with decomposition and which is converted as described in Example 12 into the corresponding free acid melting at 220°-223° C. with decomposition.

Sources & evidence

ORD record: ord-76c116de7fe34244a9de456a6e7d91e7
Source dataset: uspto-grants-1980_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04237136

Reaction notes

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