Acetic Acid → HCID 70212465, compound

HRID 380191Notes

Reaction equation

HRID 380191 reaction equation
C([C:3]1[CH:4]=[CH:5][C:6]2[S:10][C:9]([C:11]3[C:23]4[CH2:22][C:21]5[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=5)[C:15]=4C=CC=3)=[N:8][C:7]=2[C:24]=1CC)C.[N+:27]([O-:30])(O)=[O:28].[N+](C1S[C:36]2[CH:42]=[CH:41][CH:40]=[CH:39]C=2N=1)([O-])=O.[C:43](O)(=O)[CH3:44]>>[CH2:43]([C:41]1([CH2:40][CH3:39])[C:42]2[CH:36]=[C:11]([C:9]3[S:10][C:6]4[CH:5]=[CH:4][CH:3]=[CH:24][C:7]=4[N:8]=3)[CH:23]=[CH:15][C:16]=2[C:17]2[C:22]1=[CH:21][C:20]([N+:27]([O-:30])=[O:28])=[CH:19][CH:18]=2)[CH3:44]

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 944Nitric AcidHCID 640709benzothiazole, 2-nitro-HCID 70211764HCID 70211764, compound

Product 1

HCID 70212465HCID 70212465, compound

Conditions

Temperature
232.5500030517578 °C

Procedure

A mixture of diethylfluorenyl benzothiazole, (9.0 g.), acetic acid (75 ml), and conc. nitric acid (sp. gr. 1.42, 25 ml) was held at 105° C. for 2 hours, cooled and filtered. These solids were stirred in dilute sodium hydroxide solution and filtered to get 10 g. of crude solid. This was recrystallized from toluene-heptane to afford 7.58 g., 75% of the nitrobenzothiazole, m.p. 209-2140C. Mass Spec: (m/z) 400(M+). Two recrystallizations from toluene-heptane raised the m.p. to 231.6-233.5° C. Anal. Calcd. for C24H20N2O2S: C, 71.98; H, 5.03; N, 7.00; S, 7.99. Found: C, 71.70, H, 4.90; N, 6.62; S, 7.77.

Workup

  1. temperaturecooled
  2. filtrationfiltered
  3. filtrationfiltered
  4. customto get 10 g
  5. customThis was recrystallized from toluene-heptane
  6. customto afford 7.58 g
  7. customTwo recrystallizations from toluene-heptane

Sources & evidence

ORD record
ord-0f4a840795ac44aeb482a184e7aa2c69
Source dataset
uspto-grants-2001_10
Patent number
US06300502B1

Reaction notes

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