Hydrochloric Acid → 2-Amino-5-nitrobenzenethiol

HRID 1917141Notes

Reaction equation

HRID 1917141 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]2[N:8]=C[S:10][C:6]=2[CH:5]=1)([O-:3])=[O:2].O.NN.Cl>C(O)C.O>[NH2:8][C:7]1[CH:11]=[CH:12][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][C:6]=1[SH:10]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 24654Hydrazine hydrate (1:1)HCID 762566-Nitrobenzothiazole

Product 1

HCID 109866912-Amino-5-nitrobenzenethiol

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a stirred suspension of 6-nitrobenzo[d]thiazole (1.64 g, 9.10 mmol) in ethanol (16 mL) was added hydrazine hydrate (2.66 mL, 54.6 mmol). The resulting dark solution was stirred overnight at room temperature. The mixture was then diluted with water and slowly acidified with 3 M HCl, giving a yellow suspension. The mixture was then extracted with dichloromethane. The combined organics were dried, filtered, and concentrated, giving a yellow solid, used directly in the subsequent reaction. 1H NMR (DMSO-d6) δ 8.09 (brs, 1H), 7.87 (d, J=8.7 Hz, 1H), 6.74 (d, J=9.0 Hz, 1H), 6.27 (brs, 2H); MS-EI: (m/z, %) 170 (M+, 100), 140 (28), 124 (35).

Workup

  1. customgiving a yellow suspension
  2. extractionThe mixture was then extracted with dichloromethane
  3. customThe combined organics were dried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customgiving a yellow solid
  7. customused directly in the subsequent reaction

Sources & evidence

ORD record
ord-982005ca70b64de6bbd07a5c8dda71a4
Source dataset
uspto-grants-2013_12
Patent number
US08618286B2

Reaction notes

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