Diisopropylethylamine → 2-(2-(5-(4-Chlorophenyl)-2,3-dihydro-1,3,4-thiadiazol-2-yl)phenoxy)acetamide

HRID 1694338Notes

Reaction equation

HRID 1694338 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([NH:8][NH2:9])=[S:7])=[CH:4][CH:3]=1.[CH:12]([C:14]1[CH:24]=[CH:23][CH:22]=[CH:21][C:15]=1[O:16][CH2:17][C:18]([NH2:20])=[O:19])=O.CCN(C(C)C)C(C)C>C(Cl)Cl>[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]2[S:7][CH:12]([C:14]3[CH:24]=[CH:23][CH:22]=[CH:21][C:15]=3[O:16][CH2:17][C:18]([NH2:20])=[O:19])[NH:9][N:8]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 27592282-(2-Formylphenoxy)acetamideHCID 124770754-Chloro-thiobenzoic acid hydrazide

Product 1

HCID 672793222-(2-(5-(4-Chlorophenyl)-2,3-dihydro-1,3,4-thiadiazol-2-yl)phenoxy)acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a heterogeneous mixture of 4-chloro-thiobenzoic acid hydrazide (1.3 mmol) in 12 mL of CH2Cl2 is added 2-(2-formylphenoxy)acetamide (1.53 mmol) and DIEA (1.53 mmol). After 10 minutes the mixture become homogenous and the reaction is complete by TLC and LCMS to give 2-(2-(5-(4-chlorophenyl)-2,3-dihydro-1,3,4-thiadiazol-2-yl)phenoxy)-acetamide which is used as such in the next step without evaporation of the solvent.

Sources & evidence

ORD record
ord-449f8337c51b431f8747b3aa8e6b2ef4
Source dataset
uspto-grants-2012_04
Patent number
US08158662B2

Reaction notes

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