Water → HCID 21877972, compound

HRID 896158Notes

Reaction equation

HRID 896158 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[CH:4][C:3]=1[C:11]1[S:12][CH2:13][C:14](=[O:17])[NH:15][N:16]=1.O.[Cl-].[NH4+].ClCCl>C(O)C.[Fe]>[NH2:8][C:6]1[CH:5]=[CH:4][C:3]([C:11]2[S:12][CH2:13][C:14](=[O:17])[NH:15][N:16]=2)=[C:2]([F:1])[CH:7]=1

Participants

7

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 25517Ammonium ChlorideHCID 21877911HCID 21877911, compound

Product 1

HCID 21877972HCID 21877972, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

2-(2-Fluoro-4-nitrophenyl)-4H-[1,3,4]thiadiazin-5-one (Step 4, 0.964 g, 0.00378 mol) is heated in ethanol (20 ml) until dissolved. Water (10 ml) and ammonium chloride (2.02 g, 0.0378 mol) are added and the mixture heated to 90° C. Iron powder (0.84 g, 0.0151 mol) is added portionwise and the mixture stirred and heated for 30 minutes. The reaction is cooled and dichloromethane (100 ml) added. The mixture is filtered and the organic layer separated, washed with saline, dried (MgSO4) and evaporated to give the title compound as a yellow solid (0.78 g, 92%), [M+H]+=226.

Workup

  1. dissolutionuntil dissolved
  2. temperatureheated for 30 minutes
  3. temperatureThe reaction is cooled
  4. filtrationThe mixture is filtered
  5. customthe organic layer separated
  6. washwashed with saline
  7. dry with materialdried (MgSO4)
  8. customevaporated

Sources & evidence

ORD record
ord-f44ffd67e1f74581b0f02167d63e2bca
Source dataset
uspto-grants-2005_07
Patent number
US06919329B2

Reaction notes

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