Dimethylformamide dimethyl acetal → HCID 178484240, compound

HRID 2284626Notes

Reaction equation

HRID 2284626 reaction equation
[NH2:1][C:2]1[N:3]=[N:4][C:5]([Br:8])=[CH:6][CH:7]=1.CO[CH:11](OC)[N:12]([CH3:14])[CH3:13]>>[Br:8][C:5]1[N:4]=[N:3][C:2](/[N:1]=[CH:11]/[N:12]([CH3:14])[CH3:13])=[CH:7][CH:6]=1

Participants

3

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 27947796-Bromopyridazin-3-amine

Product 1

HCID 178484240HCID 178484240, compoundYield 74.5%

Procedure

3-Amino-6-bromopyridazine (5.0 g, 28.7 mmol) was heated and stirred with dimethylformamide dimethylacetal (5.36 g, 6.0 mL, 45.0 mmol) under nitrogen at 110° C. for 3 h. The brown homogeneous reaction mixture was cooled to room temperature. The resulting heterogeneous slurry was stirred in EtOAc/hexanes (1:1, 75 mL) and filtered. The filtered solid was suction dried to obtain apparently (E)-N′-(6-bromopyridazin-3-yl)-N,N-dimethylformimidamide (4.9 g) as a pale pink crystalline solid. 1H NMR (300 MHz, DMSO-d6) δ 8.45 (s, 1H), 7.64 (d, J=9.1 Hz, 1H), 7.03 (d, J=9.1 Hz, 1H), 3.11 (s, 3H), 3.00 (s, 3H).

Workup

  1. filtrationfiltered
  2. customdried

Sources & evidence

ORD record
ord-3a6bfbd691de477abcfc45c000071a63
Source dataset
uspto-grants-2015_09
Patent number
US09145433B2

Reaction notes

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