Benzyl((5-(4-(benzyloxy)phenyl)-1,3,4-thiadiazol-2-yl)methyl)carbamate → 4-(5-(Aminomethyl)-1,3,4-thiadiazol-2-yl)phenol

HRID 445398Notes

Reaction equation

HRID 445398 reaction equation
C(OC(=O)[NH:10][CH2:11][C:12]1[S:13][C:14]([C:17]2[CH:22]=[CH:21][C:20]([O:23]CC3C=CC=CC=3)=[CH:19][CH:18]=2)=[N:15][N:16]=1)C1C=CC=CC=1>Br.C(O)(=O)C.C(OCC)C>[NH2:10][CH2:11][C:12]1[S:13][C:14]([C:17]2[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=2)=[N:15][N:16]=1

Participants

5

Reactant 1

HCID 123333842Benzyl((5-(4-(benzyloxy)phenyl)-1,3,4-thiadiazol-2-yl)methyl)carbamate

Product 1

HCID 1363406864-(5-(Aminomethyl)-1,3,4-thiadiazol-2-yl)phenol

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 260Hydrogen BromideSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of benzyl((5-(4-(benzyloxy)phenyl)-1,3,4-thiadiazol-2-yl)methyl)carbamate (7.4 g, 17.1 mmol) in 33% HBr in acetic acid (100 mL) and was stirred for 2 h. The resulting mixture was diluted with diethyl ether and the precipitate was collected and washed with diethyl ether to yield 4-(5-(aminomethyl)-1,3,4-thiadiazol-2-yl)phenol (MS m/z=408 MH+).

Workup

  1. customthe precipitate was collected
  2. washwashed with diethyl ether

Sources & evidence

ORD record
ord-62ecadd3cac4401d8591de3ba42f70fe
Source dataset
uspto-grants-2013_07
Patent number
US08476302B2

Reaction notes

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