Hydrochloric Acid → 2-Amino-5-nitrobenzenethiol

HRID 424497Notes

Reaction equation

HRID 424497 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-nitrobenzenethiolYield 98%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

To a suspension of 6-nitrobenzo[d]thiazole (5 g, 27.7 mmol) in ethanol (45 mL) was added hydrazine hydrate (8.10 mL, 166 mmol). The resulting mixture (dark red) was stirred overnight at room temperature. The mixture was then acidified by the slow, careful addition of 3M HCl in water (50 mL). This mixture was further diluted with water (50 mL), and the resulting yellow/orange precipitate was extracted with dichloromethane (3×). The combined organics were dried, filtered, and concentrated, giving an orange solid (4.62 g, 98%). 1H NMR (DMSO-d6) δ 8.12-8.09 (m, 1H), 7.88-7.85 (m, 1H), 6.75-6.71 (m, 1H), 6.28 (brs, 2H); ESI-MS (m/z, %): 170 (MH+, 100).

Workup

  1. extractionthe resulting yellow/orange precipitate was extracted with dichloromethane (3×)
  2. customThe combined organics were dried
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-837a6c0f7fd6497fba539c796ca178cf
Source dataset
uspto-grants-2012_01
Patent number
US08106043B2

Reaction notes

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