Water → 4-Amino-3-nitrophenyl thiocyanate

HRID 1758880Notes

Reaction equation

HRID 1758880 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].[NH4+].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 15666Ammonium thiocyanateHCID 24408Bromine

Product 1

HCID 1046774-Amino-3-nitrophenyl thiocyanate

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To a well-stirred mixture of 108 g of o-nitroaniline and 128 g of ammonium thiocyanate in 400 ml of acetic acid there is added dropwise a solution of 128 g of bromine in 160 ml of acetic acid below 20° C. The mixture is stirred for 4 hours at room temperature and then poured into 4 liters of water. The resulting solid is filtered off and crystallized from ethanol to yield 86.7 g, m.p. 111°-114° C.

Workup

  1. filtrationThe resulting solid is filtered off
  2. customcrystallized from ethanol
  3. customto yield 86.7 g, m.p. 111°-114° C.

Sources & evidence

ORD record
ord-2d257c1e90464497ba8a273ae4fdc316
Source dataset
uspto-grants-1982_07
Patent number
USRE030990

Reaction notes

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