Water → 4-Amino-3-nitrophenyl thiocyanate

HRID 1834799Notes

Reaction equation

HRID 1834799 reaction equation
[N+:1]([C:4]1[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=1[NH2:6])([O-:3])=[O:2].[S-:11][C:12]#[N:13].[Na+].BrBr.O>C(O)(=O)C>[N+:1]([C:4]1[CH:10]=[C:9]([S:11][C:12]#[N:13])[CH:8]=[CH:7][C:5]=1[NH2:6])([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 962WaterHCID 69462-NitroanilineHCID 24408BromineHCID 516871Sodium thiocyanate

Product 1

HCID 1046774-Amino-3-nitrophenyl thiocyanateYield 91.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Conditions

Temperature
15 °C

Procedure

A stirred mixture of o-nitroaniline (82.5 g), dry sodium thiocyanate (180 g) and acetic acid (1 liter) was treated at 11°-12° C with a solution of bromine (96.5 g) in acetic acid (100 ml). The stirring was continued for a further hour at 11°-12° C and the mixture was then allowed to warm to 15° C and poured into water (3.5 liters). The yellow solid was filtered off, washed with water, and dissolved in acetone (1 liter). The solution was filtered and the filtrate was evaporated to give 2-nitro-4-thiocyanatoaniline (107 g), m.p. 110°-112° C.

Workup

  1. waitThe stirring was continued for a further hour at 11°-12° C
  2. filtrationThe yellow solid was filtered off
  3. washwashed with water
  4. dissolutiondissolved in acetone (1 liter)
  5. filtrationThe solution was filtered
  6. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-f6e37cfa356d477a858454eda7e74a9f
Source dataset
uspto-grants-1978_01
Patent number
US04071528

Reaction notes

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