Dimethylformamide → HCID 11161046, compound

HRID 985415Notes

Reaction equation

HRID 985415 reaction equation
O[CH2:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([NH:9][C:10]2[S:11][C:12]([C:15]#[N:16])=[CH:13][N:14]=2)[CH:4]=1.CN(C)C=O.P(Cl)(Cl)([Cl:24])=O>C(Cl)Cl>[Cl:24][CH2:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([NH:9][C:10]2[S:11][C:12]([C:15]#[N:16])=[CH:13][N:14]=2)[CH:4]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 11299219HCID 11299219, compound

Product 1

HCID 11161046HCID 11161046, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-(4-Hydroxymethyl-pyridin-2-ylamino)-thiazole-5-carbonitrile (0.883 g, 3.80 mmol) was stirred in anhydrous CH2Cl2 (12 mL) under N2. Dimethylformamide (0.354 mL, 3.80 mmol, 1 equiv) was added followed by the addition of phosphorous oxychloride (0.294 mL, 3.80 mmol). After 4 hours the reaction was concentrated and quenched by the addition of saturated NaHCO3 (aq). A precipitate formed which was filtered and washed with water to provide the titled compound. 1H NMR (DMSO-d6) δ 12.35 (bs, 1H), 8.40 (d, 1H, J=5.3 Hz), 8.28 (s, 1H), 7.20 (s, 1H), 7.12 (d, 1H, J=5.3 Hz), 4.82 (s, 2H).

Workup

  1. concentrationAfter 4 hours the reaction was concentrated
  2. customquenched by the addition of saturated NaHCO3 (aq)
  3. customA precipitate formed which
  4. filtrationwas filtered
  5. washwashed with water

Sources & evidence

ORD record
ord-17907e1c513843958dfcc7adb258f097
Source dataset
uspto-grants-2005_03
Patent number
US06872724B2

Reaction notes

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