Acetyl chloride → HCID 60207454, compound

HRID 1192235Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:26])[C:7]=1[S:8][C:9]1[S:13][C:12]([C:14]([NH:16][CH:17]2[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]2)=[O:15])=[CH:11][C:10]=1[N+:23]([O-:25])=[O:24].[C:27](Cl)(=[O:29])[CH3:28]>>[C:27]([N:20]1[CH2:21][CH2:22][CH:17]([NH:16][C:14]([C:12]2[S:13][C:9]([S:8][C:7]3[C:6]([Cl:26])=[CH:5][N:4]=[CH:3][C:2]=3[Cl:1])=[C:10]([N+:23]([O-:25])=[O:24])[CH:11]=2)=[O:15])[CH2:18][CH2:19]1)(=[O:29])[CH3:28]

Participants

Reactant 2

HCID 6367Acetyl chloride

HCID 60207455HCID 60207455, compound

Product 1

HCID 60207454HCID 60207454, compound

Procedure

Prepared according to the procedure described for example 199 from 5-((3,5-dichloropyridin-4-yl)thio)-4-nitro-N-(piperidin-4-yl)thiophene-2-carboxamide (0.2 g, 0.46 mmol) and acetyl chloride (53.0 mg, 0.69 mmol). The title compound was obtained as a solid (75 mg, 35% yield). 1H NMR (400 MHz, d6-DMSO) δ:8.98 (2H, m), 8.67 (1H, m), 8.48 (1H, s), 4.28 (1H, m), 3.89 (1H, m), 3.80 (1H, m), 3.61 (1H, m), 3.13 (1H, m), 2.70 (1H, m), 2.00 (3H, s), 1.83 (1H, m), 1.76 (1H, m), 1.41 (1H, m), 1.28 (1H, m). MS m/z: 473.23, 475.25 [M+H]+.

Workup

customPrepared

Sources & evidence

ORD record: ord-b85c082b8a8341fdb08a442641357ed4
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08680139B2

Reaction notes

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