Thionyl Chloride → HCID 86634856, compound

HRID 628055Notes

Reaction equation

HRID 628055 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12](=[O:13])[N:11]([CH3:14])[N:10]=[C:9]1[C:15]1[S:31][C:18]2[C:19]3[CH:27]=[CH:26][C:25]([C:28]([OH:30])=O)=[CH:24][C:20]=3[O:21][CH2:22][CH2:23][C:17]=2[CH:16]=1.O=S(Cl)[Cl:34]>>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12](=[O:13])[N:11]([CH3:14])[N:10]=[C:9]1[C:15]1[S:31][C:18]2[C:19]3[CH:27]=[CH:26][C:25]([C:28]([Cl:34])=[O:30])=[CH:24][C:20]=3[O:21][CH2:22][CH2:23][C:17]=2[CH:16]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 866348572-(4-(2-chlorophenyl)-1-methyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-8-carboxylic acid

Product 1

HCID 86634856HCID 86634856, compound

Procedure

A solution of 2-(4-(2-chlorophenyl)-1-methyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-8-carboxylic acid (300 mg, 0.66 mmol) in 10 mL of SOCl2 was heated at 80° C. for 3 h. Concentration gave the crude acid chloride, 2-(4-(2-chlorophenyl)-1-methyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-8-carbonyl chloride which was slowly added (ca. 312 mg, ca. 0.66 mmol in 10 mL of THF), to a solution of NH3 (saturated solution in THF) and pyridine (0.5 mL) in 5 mL of THF at 0° C. The mixture was stirred at room temperature overnight, Diluted with water, the solids were washed with water and dried in vacuum. The crude product was purified by HPLC separation, gave 160.1 mg of 363, isolated yield: 54%. ESI-MS: 453. 1H NMR (DMSO-d6, 400 MHz): δ 7.98-7.41 (m, 9H, ArH, NH2), 6.49 (s, 1H, ═CH), 4.20 (s, 2H, CH2), 3.49 (s, 3H, CH3), 2.99 (s, 2H, CH2).

Workup

  1. concentrationConcentration

Sources & evidence

ORD record
ord-3c9d5245d43f415fb47305a808bffed9
Source dataset
uspto-grants-2016_04
Patent number
US09309265B2

Reaction notes

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