Dimethylamine → HCID 59525931, compound

HRID 385744Notes

Reaction equation

HRID 385744 reaction equation
Cl[CH:2](Cl)[C:3]1[CH:4]=[C:5]([C:11]2[N:15]=[CH:14][N:13]([CH2:16][O:17][CH2:18][CH2:19][Si:20]([CH3:23])([CH3:22])[CH3:21])[N:12]=2)[S:6][C:7]=1[N+:8]([O-:10])=[O:9].N(C)C.[OH2:28]>>[N+:8]([C:7]1[S:6][C:5]([C:11]2[N:15]=[CH:14][N:13]([CH2:16][O:17][CH2:18][CH2:19][Si:20]([CH3:23])([CH3:22])[CH3:21])[N:12]=2)=[CH:4][C:3]=1[CH:2]=[O:28])([O-:10])=[O:9]

Participants

4

Reactant 3

HCID 674DimethylamineHCID 962WaterHCID 59526358HCID 59526358, compound

Product 1

HCID 59525931HCID 59525931, compound

Conditions

Temperature
60 °C

Procedure

A mixture of 3-[4-(dichloromethyl)-5-nitro-2-thienyl]-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-1,2,4-triazole (1.00 g, 2.44 mmol) and Me2NH (40% wt, 15.00 mL, 118 mmol) was stirred at 60° C. for 15 min. The reaction was cooled to room temperature, diluted with water, and extracted with CH2Cl2 (2×). The combined organic layers were dried (MgSO4), filtered, and evaporated. Purification of the crude residue by flash chromatography (0-50% EtOAc/hexanes) provided the title compound as a yellow solid.

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. extractionextracted with CH2Cl2 (2×)
  3. dry with materialThe combined organic layers were dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. customPurification of the crude residue by flash chromatography (0-50% EtOAc/hexanes)

Sources & evidence

ORD record
ord-0997c0fad4c14fc78ddd5ccb51473296
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

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