Acetic Anhydride → HCID 178474512, compound

HRID 1517672Notes

Reaction equation

HRID 1517672 reaction equation
[C:1]([O-:4])(=O)[CH3:2].[Na+].[N+:6]([C:9]1[CH:18]=[C:17]2[C:12]([CH2:13][CH2:14][C:15](=O)[CH2:16]2)=[CH:11][CH:10]=1)([O-:8])=[O:7].BrBr.[NH2:22][C:23]([NH2:25])=[S:24].C(OC(=O)C)(=O)C>C(O)(=O)C>[N+:6]([C:9]1[CH:18]=[C:17]2[C:12]([CH2:13][CH2:14][C:15]3[NH:22][C:23]([NH:25][C:1](=[O:4])[CH3:2])=[SH:24][C:16]=32)=[CH:11][CH:10]=1)([O-:8])=[O:7]

Participants

7

Reactant 5

HCID 7918Acetic AnhydrideHCID 24408Bromine2×HCID 517045Sodium AcetateHCID 2723790ThioureaHCID 113214437-Nitro-2-tetralone

Product 1

HCID 178474512HCID 178474512, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
15 °C

Procedure

0.8 g (10.0 mmol) sodium acetate and 1.9 g (9.40 mmol) 7-nitro-3,4-dihydro-1H-naphthalen-2-one (prepared according to D. E. Nichols et al., J. Med. Chem. 1989, 32, 2128-2134) are dissolved in 40 ml acetic acid and cooled to 15° C. 0.5 g (3.19 mmol) bromine are added and the mixture is stirred for 0.1 hours, until the bromine has finished reacting completely. Then 0.8 g (10.5 mmol) thiourea are added. The reaction mixture is heated to 60° C. for 0.25 hours, then suction filtered and washed. The crystals are recrystallised from ethanol. Yield: 0.75 g (M.p.: 247-248° C.) 0.75 g (3.0 mmol) of the compound described previously are placed in 5 ml (49 mmol) acetic anhydride and refluxed for 0.1 hours. After cooling to ambient temperature the precipitate formed is suction filtered, washed with ethyl acetate and diethyl ether and dried. Yield: 0.8 g (M.p.: >315° C.)

Workup

  1. temperatureThe reaction mixture is heated to 60° C. for 0.25 hours
  2. filtrationsuction filtered
  3. washwashed
  4. customThe crystals are recrystallised from ethanol
  5. temperaturerefluxed for 0.1 hours
  6. temperatureAfter cooling to ambient temperature the precipitate
  7. customformed
  8. filtrationfiltered
  9. washwashed with ethyl acetate and diethyl ether
  10. customdried

Sources & evidence

ORD record
ord-bb08ce5d0bf94d5fb721057577350872
Source dataset
uspto-grants-2012_07
Patent number
US08232286B2

Reaction notes

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