Water → HCID 9899528, compound

HRID 1465813Notes

Reaction equation

HRID 1465813 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([CH:8]=1)[NH2:7].[NH:12]1[CH2:17][CH2:16][S:15][CH2:14][CH2:13]1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C(=O)C>[N+:9]([C:5]1[CH:4]=[CH:3][C:2]([N:12]2[CH2:17][CH2:16][S:15][CH2:14][CH2:13]2)=[CH:8][C:6]=1[NH2:7])([O-:11])=[O:10]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 67164ThiomorpholineHCID 742185-Chloro-2-nitroaniline

Product 1

HCID 9899528HCID 9899528, compoundYield 91.5%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
135 °C

Procedure

A mixture of 5-chloro-2-nitroaniline (5.6 g, 32 mmol), thiomorpholine (10.0 g, 97 mmol) and anhydrous potassium carbonate (4.98 g, 36 mmol) in N,N-dimethylacetamide (10 ml) was stirred at 135° C. under nitrogen for 1 day. Sample NMR analysis showed complete conversion of the starting material. The resultant mixture was then cooled to room temperature, poured into cold water and stirred vigorously for 3 hours. The resulting brown precipitate was collected by filtration, washed well with water then dried on the filter funnel. The resulting brown solid was washed with diethyl ether, filtered, washed with additional diethyl ether, dried to afford 2-Nitro-5-thiomorpholin-4-yl-phenylamine (7.0 g, 91.5%) as a brown powder, and used in the next step without further purification.

Workup

  1. stirringstirred vigorously for 3 hours
  2. filtrationThe resulting brown precipitate was collected by filtration
  3. washwashed well with water
  4. customthen dried on the filter funnel
  5. washThe resulting brown solid was washed with diethyl ether
  6. filtrationfiltered
  7. washwashed with additional diethyl ether
  8. customdried

Sources & evidence

ORD record
ord-cb750fa9250c4c9f884311217e0736f9
Source dataset
uspto-grants-2015_04
Patent number
US08999993B2

Reaction notes

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