Hydrochloric Acid → 2-Chloro-6-nitrobenzothiazole

HRID 1174888Notes

Reaction equation

HRID 1174888 reaction equation
N(OC(C)(C)C)=O.N[C:9]1[S:10][C:11]2[CH:17]=[C:16]([N+:18]([O-:20])=[O:19])[CH:15]=[CH:14][C:12]=2[N:13]=1.[ClH:21]>C(#N)C.C(Cl)Cl.[Cu](Cl)Cl>[Cl:21][C:9]1[S:10][C:11]2[CH:17]=[C:16]([N+:18]([O-:20])=[O:19])[CH:15]=[CH:14][C:12]=2[N:13]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 10906Tert-Butyl nitriteHCID 227042-Amino-6-nitrobenzothiazole

Product 1

HCID 754762-Chloro-6-nitrobenzothiazoleYield 77%

Reagents, catalysts & solvents 3

HCID 24014Cupric ChlorideCatalystHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
65 °C

Procedure

Combine tert-butyl nitrite, (35 mL, 292 mmol, technical 90%) and copper (II) chloride (31.7 g, 236 mmol) in acetonitrile (400 mL) and warm to 65° C. under nitrogen for 1 hour. Slowly add 2-amino-6-nitrobenzthiazole (41.7 g, 214 mmol) over 15 min. Continue to stir at 65° C. for 30 min. Cool to room temperature, dilute with CH2Cl2, and add 0.1 N HCl to precipitate the product. Filter and dry in a vacuum oven overnight to afford 2-chloro-6-nitrobenzthiazole (35.1 g, 77%). 1H NMR (400 MHz, DMSO-d6): δ 9.18 (d, 1H, J=2.2 Hz), 8.37 (dd, 1H, J=9.0, 2.4 Hz), 8.18 (d, 1H, J=8.8 Hz).

Workup

  1. temperatureCool to room temperature
  2. customto precipitate the product
  3. filtrationFilter
  4. customdry in a vacuum oven overnight

Sources & evidence

ORD record
ord-2f6d1c2795e64b84ad8863c988147ed7
Source dataset
uspto-grants-2010_11
Patent number
US07838543B2

Reaction notes

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