Dimethylamine → HCID 25230881, compound

HRID 2272937Notes

Reaction equation

HRID 2272937 reaction equation
Cl[C:2]1[S:10][C:9]2[C:8]([C:11]([C:13]3[S:14][CH:15]=[CH:16][CH:17]=3)=[O:12])=[N:7][C:6]([NH:18][CH2:19][C:20]3[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=3)=[N:5][C:4]=2[CH:3]=1.[CH3:26][NH:27][CH3:28].O>CC(N(C)C)=O>[CH3:26][N:27]([CH3:28])[C:2]1[S:10][C:9]2[C:8]([C:11]([C:13]3[S:14][CH:15]=[CH:16][CH:17]=3)=[O:12])=[N:7][C:6]([NH:18][CH2:19][C:20]3[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=3)=[N:5][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 674DimethylamineHCID 962WaterHCID 46883208HCID 46883208, compound

Product 1

HCID 25230881HCID 25230881, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
170 °C

Procedure

A stirred solution of Example 5 (0.02 g, 0.052 mmol) in dimethylacetamide (1.5 ml) was treated with dimethylamine (2.0M in THF, 0.52 mmol). The solution was heated to 170° C. for 30 min in a microwave reactor. The cooled solution was poured onto stirred iced water (20 ml). After 15 min stirring, an orange solid was filtered. Recrystallisation from hot ethyl acetate gave the title compound in 42% yield, >95% purity. LC-MS m/z=396.0 [M+H]+; RT=2.97; LC-MS method 1. 1H NMR: δH (400 MHz, D6-DMSO) 3.13 (6H, s), 4.68 (2H, bd), 5.91 (1H, s), 7.26-8.61 (8H, m).

Workup

  1. additionThe cooled solution was poured
  2. filtrationan orange solid was filtered
  3. customRecrystallisation from hot ethyl acetate

Sources & evidence

ORD record
ord-b497a53eaf554f35bf640d91194d4bd6
Source dataset
uspto-grants-2015_09
Patent number
US09120807B2

Reaction notes

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