Pendimethalin → HCID 54403400, compound

HRID 1388084Notes

Reaction equation

HRID 1388084 reaction equation
[CH2:1]([CH:3]([NH:6][C:7]1[C:12]([N+:13]([O-:15])=[O:14])=[CH:11][C:10]([CH3:16])=[C:9]([CH3:17])[C:8]=1[N+:18]([O-:20])=[O:19])[CH2:4][CH3:5])[CH3:2].CO[CH:23](OC)[N:24]([CH3:26])[CH3:25]>>[CH2:1]([CH:3]([NH:6][C:7]1[C:8]([N+:18]([O-:20])=[O:19])=[C:9]([C:10]([CH3:16])=[CH:11][C:12]=1[N+:13]([O-:15])=[O:14])[CH:17]=[CH:23][N:24]([CH3:26])[CH3:25])[CH2:4][CH3:5])[CH3:2]

Participants

3

Reactant 2

HCID 38479PendimethalinHCID 78373Dimethylformamide dimethyl acetal

Product 1

HCID 54403400HCID 54403400, compound

Conditions

Temperature
85 °C

Procedure

A mixture of N-(1-ethylpropyl)-2,6-dinitro-3,4-xylidine (50.0 g; 0.18 mol) and dimethylformamide dimethyl acetal (125 ml) is stirred at 85° C. overnight. The temperature of the reaction mixture is then raised to 90°-100° C. and methanol distilled off until approximately 12.5 ml methanol is collected. The reaction mixture is then cooled down, poured into hexane (400 ml) and chilled. The crystallized red solid (45.6 g; 75.3%) is collected and air dried. A sample is purified for analysis, melting point 100°-102° C.

Workup

  1. temperatureThe temperature of the reaction mixture is then raised to 90°-100° C.
  2. distillationmethanol distilled off until approximately 12.5 ml methanol
  3. customis collected
  4. temperatureThe reaction mixture is then cooled down
  5. additionpoured into hexane (400 ml)
  6. temperaturechilled
  7. customThe crystallized red solid (45.6 g; 75.3%) is collected
  8. customair dried
  9. customA sample is purified for analysis, melting point 100°-102° C.

Sources & evidence

ORD record
ord-0af855b012474146abcb18e187b6b740
Source dataset
uspto-grants-1984_02
Patent number
US04430114

Reaction notes

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