2-Methoxybenzoyl chloride → HCID 59026631, compound

HRID 333705Notes

Reaction equation

HRID 333705 reaction equation
[NH2:1][C:2]1[CH:6]=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=2)[S:4][C:3]=1[C:14]#[N:15].[CH3:16][O:17][C:18]1[CH:26]=[CH:25][CH:24]=[CH:23][C:19]=1[C:20](Cl)=[O:21]>N1C=CC=CC=1>[C:14]([C:3]1[S:4][C:5]([C:7]2[CH:8]=[CH:9][C:10]([F:13])=[CH:11][CH:12]=2)=[CH:6][C:2]=1[NH:1][C:20](=[O:21])[C:19]1[CH:23]=[CH:24][CH:25]=[CH:26][C:18]=1[O:17][CH3:16])#[N:15]

Participants

4

Reactant 2

HCID 889692-Methoxybenzoyl chlorideHCID 27358943-Amino-5-(4-fluorophenyl)thiophene-2-carbonitrile

Product 1

HCID 59026631HCID 59026631, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 3-amino-5-(4-fluorophenyl)thiophene-2-carbonitrile (2.0 g, 9.2 mmol) in pyridine (40 mL) was cooled in an ice bath, and 2-methoxybenzoyl chloride (1.2 mL, 9.2 mmol) was added dropwise. The cooling bath was removed, and the reaction was stirred for 16 h. The reaction was poured into water, and the resulting suspension was acidified with 1 M hydrochloric acid. The solid was filtered, washed with water, and dried under vacuum to give N-(2-cyano-5-(4-fluorophenyl)thiophen-3-yl)-2-methoxybenzamide (2.4 g, 74% yield).

Workup

  1. customThe cooling bath was removed
  2. additionThe reaction was poured into water
  3. filtrationThe solid was filtered
  4. washwashed with water
  5. customdried under vacuum

Sources & evidence

ORD record
ord-30b0592c3f954f3bae612b0fd9ec7d79
Source dataset
uspto-grants-2014_11
Patent number
US08883781B2

Reaction notes

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