Benzoyl chloride → HCID 58976551, compound

HRID 1179265Notes

Reaction equation

HRID 1179265 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[S:10]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[N:12]=[C:11]1[N:19]1[C:23]([NH2:24])=[N:22][C:21]([NH2:25])=[N:20]1>N1C=CC=CC=1>[NH2:24][C:23]1[N:19]([C:11]2[S:10][C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[N:12]=2)[N:20]=[C:21]([NH:25][C:1](=[O:8])[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[N:22]=1

Participants

4

Reactant 2

HCID 7412Benzoyl chlorideHCID 58976966HCID 58976966, compound

Product 1

HCID 58976551HCID 58976551, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Benzoyl chloride (0.34 mmol) was added dropwise to a stirred solution of 1-benzothiazol-2-yl-1H-[1,2,4]triazole-3,5-diamine (0.34 mmol) in pyridine (3 ml). The reaction mixture was stirred at room temperature for 2 hours then it was concentrated in vacuo. The residue was partitionned between ethyl acetate and 10% aqueous citric acid. At this stage, a white solid was filtered off. The solid was dried in vacuo to afford the pure title compound (10 mg; 15% yield). 1H (400 MHz, DMSO-d6) δ 7.40-7.45 (1H, t), 7.50-7.70 (3H, m), 7.85-8.00 (6H, m), 8.1 (1H, d), 10.95 (1H, s). MS (ES+) m/e=337

Workup

  1. concentrationit was concentrated in vacuo
  2. filtrationAt this stage, a white solid was filtered off
  3. customThe solid was dried in vacuo

Sources & evidence

ORD record
ord-7ce86c996079487b9cfacd4e9e0398a1
Source dataset
uspto-grants-2007_10
Patent number
US07279469B2

Reaction notes

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