Trifluoroacetic acid → 4-amino-N-(5-benzyl[1.3.4]thiadiazol-2-yl)-benzamide

HRID 1035702Notes

Reaction equation

HRID 1035702 reaction equation
[CH2:1]([C:8]1[S:12][C:11]([NH:13][C:14]([C:16]2[CH:21]=[CH:20][C:19]([NH:22]C(=O)OC(C)(C)C)=[CH:18][CH:17]=2)=[O:15])=[N:10][N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>ClCCl>[NH2:22][C:19]1[CH:20]=[CH:21][C:16]([C:14]([NH:13][C:11]2[S:12][C:8]([CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[N:9][N:10]=2)=[O:15])=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86662112Tert-butyl [4-(5-benzyl[1.3.4]thiadiazol-2-ylcarbamoyl)phenyl]carbamate

Product 1

HCID 667399484-amino-N-(5-benzyl[1.3.4]thiadiazol-2-yl)-benzamideYield 92.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.2 g of tert-butyl [4-(5-benzyl[1.3.4]thiadiazol-2-ylcarbamoyl)phenyl]carbamate (0.49 mmol, 1 eq.) is placed in 5 mL of dichloromethane. 1 mL of trifluoroacetic acid (13.54 mmol, 27.6 eq.) is added and the reaction medium is stirred for 3 days at room temperature. The solvents are evaporated off and the residue is taken up in diethyl ether and pentane to give 0.14 g of 4-amino-N-(5-benzyl[1.3.4]thiadiazol-2-yl)-benzamide acid.

Workup

  1. customThe solvents are evaporated off

Sources & evidence

ORD record
ord-d4284ddb46264b769d984419f915c718
Source dataset
uspto-grants-2013_10
Patent number
US08546391B2

Reaction notes

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