Nitromethane → HCID 57835770, compound

HRID 1675284Notes

Reaction equation

HRID 1675284 reaction equation
CN(C)C(N(C)C)=N.[CH3:9][O:10][C:11]1[CH:38]=[CH:37][C:14]([CH2:15][O:16][C:17]2[CH:22]=[CH:21][C:20](/[CH:23]=[CH:24]/[C:25]([O:27][CH2:28][C:29]3[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=3)=[O:26])=[CH:19][CH:18]=2)=[CH:13][CH:12]=1.[N+:39]([CH3:42])([O-:41])=[O:40]>>[CH3:9][O:10][C:11]1[CH:12]=[CH:13][C:14]([CH2:15][O:16][C:17]2[CH:18]=[CH:19][C:20]([CH:23]([CH2:42][N+:39]([O-:41])=[O:40])[CH2:24][C:25]([O:27][CH2:28][C:29]3[CH:30]=[CH:31][C:32]([O:35][CH3:36])=[CH:33][CH:34]=3)=[O:26])=[CH:21][CH:22]=2)=[CH:37][CH:38]=1

Participants

4

Reactant 3

HCID 6375NitromethaneHCID 664601,1,3,3-TetramethylguanidineHCID 57835753HCID 57835753, compound

Product 1

HCID 57835770HCID 57835770, compound

Conditions

Temperature
50 °C

Procedure

1,1,3,3-tetramethylguanidine (0.31 mL, 2.48 mmol) was added to 40.2 (5 g, 12.4 mmol) in nitromethane (20 mL). The mixture was stirred at room temperature for 3 hours, at 50° C. for 3 hours, and at 100° C. for 8 hours. Nitromethane was removed under vacuum and the crude product was purified by flash chromatography to give 40.3 (4.5 g). MS ESI (pos.) m/e: 466 (M+H). 1HNMR (CDCl3) δ 7.37 (d, 2H), 7.19 (d, 2H), 7.12 (d, 2H), 6.92 (m, 6H), 5.01 (s, 2H), 4.97 (s, 2H), 4.68 (m, 1H), 4.59 (m, 1H), 3.96 (m, 1H), 3.84 (s, 3H), 3.82 (s, 3H), 2.77 (m, 2H).

Workup

  1. waitat 100° C. for 8 hours
  2. customNitromethane was removed under vacuum
  3. customthe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-fb15ef625058437cac85db196cbe3fb2
Source dataset
uspto-grants-2011_08
Patent number
US08003648B2

Reaction notes

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