Hydrochloric Acid → 2-Amino-5-nitrobenzenethiol

HRID 424483

Reaction equation

HRID 424483 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-6c5b3c41325c4c05a926a6970d2485b8
Source dataset
uspto-grants-2012_01
Patent number
US08106043B2

Linked notes

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