Sulfuric Acid → 4-(2,4-Dichlorophenyl)-2-morpholin-4-yl-1,3-thiazole-5-carboxamide

HRID 1926631Notes

Reaction equation

HRID 1926631 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:10]=[C:11]([N:16]2[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)[S:12][C:13]=1[C:14]#[N:15].S(=O)(=O)(O)[OH:23]>O>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:10]=[C:11]([N:16]2[CH2:17][CH2:18][O:19][CH2:20][CH2:21]2)[S:12][C:13]=1[C:14]([NH2:15])=[O:23]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 592500334-(2,4-Dichlorophenyl)-2-morpholin-4-yl-1,3-thiazole-5-carbonitrile

Product 1

HCID 592500274-(2,4-Dichlorophenyl)-2-morpholin-4-yl-1,3-thiazole-5-carboxamideYield 85.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4-(2,4-dichlorophenyl)-2-morpholin-4-yl-1,3-thiazole-5-carbonitrile (30 mg, 0.088 mmol) was dissolved in sulfuric acid (0.200 mL, 3.75 mmol) and the mixture was stirred at rt for 1 hour. Water (1 mL) was added and the mixture was quenched with an excess of saturated NaHCO3. Precipitate was filtered off, washed with water and dried to afford the title compound (27 mg, 80%). LCMS: (FA) ES+, 358. 1H NMR (400 MHz, d6-DMSO) δ: 7.67 (d, 1H), 7.47 (d, 1H), 7.43 (dd, 1H), 3.72-3.69 (m, 4H), 3.44-3.42 (m, 4H).

Workup

  1. customthe mixture was quenched with an excess of saturated NaHCO3
  2. filtrationPrecipitate was filtered off
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-144cc0f9a3794ef5bec0a63b3d8893ff
Source dataset
uspto-grants-2012_05
Patent number
US08183240B2

Reaction notes

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