Dimethylformamide → HCID 86611450, compound

HRID 1865136Notes

Reaction equation

HRID 1865136 reaction equation
[C:1]([C:3]1[C:4]([C:13]2[CH:18]=[CH:17][C:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[C:25]#[N:26])=[CH:15][CH:14]=2)=[C:5]([C:10](O)=[S:11])[N:6]([CH3:9])[C:7]=1[CH3:8])#[N:2].C(Cl)(=O)C(Cl)=O.C[N:34](C=O)C.[OH-].N>C(Cl)Cl>[C:1]([C:3]1[C:4]([C:13]2[CH:18]=[CH:17][C:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[C:25]#[N:26])=[CH:15][CH:14]=2)=[C:5]([C:10]([NH2:34])=[S:11])[N:6]([CH3:9])[C:7]=1[CH3:8])#[N:2]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 21862953Ammonia hydroxideHCID 178428430HCID 178428430, compound

Product 1

HCID 86611450HCID 86611450, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirring solution of 4-cyano-3-[4-(2-cyanophenyl)phenyl]-1-methyl-5-methylthiopyrrole-2-carboxylic acid (11.0 mmol, prepared in example A-163) in methylene chloride, add oxalyl chloride (2.0 mmol) and catalytic DMF. Stir this solution for 20 minutes at room temperature and then concentrate in vacuo. Dissolve the residue in methylene chloride and ammonia hydroxide (2.0 mmol). Stir this reaction for one minute. The reaction becomes cloudy. Concentrate in vacuo. Purify the residue via radial chromatography and recrystallize using ether and hexanes to yield the title compound. MS (m/e): 373.1 (M+1) 371.0 (M−1); 1H NMR δ 7.97 (d, 1H), 7.84 (s, 2H), 7.80 (t, 1H), 7.66 (m, 3H), 7.57 (m, 3H), 3.80 (s, 3H), 2.46 (s, 3H).

Workup

  1. concentrationconcentrate in vacuo
  2. dissolutionDissolve the residue in methylene chloride
  3. stirringStir
  4. customthis reaction for one minute
  5. concentrationConcentrate in vacuo
  6. customPurify the residue via radial chromatography
  7. customrecrystallize

Sources & evidence

ORD record
ord-e82a28a61706468298310e23f8c8eb59
Source dataset
uspto-grants-2009_12
Patent number
US07625932B2

Reaction notes

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