Water → HCID 18552227, compound

HRID 2298718Notes

Reaction equation

HRID 2298718 reaction equation
[Cl-].[NH4+].[CH2:3]([S:19][CH2:20][C:21]1[CH:26]=[CH:25][C:24]([N+:27]([O-])=O)=[CH:23][CH:22]=1)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].O>[Fe].CO>[CH2:3]([S:19][CH2:20][C:21]1[CH:26]=[CH:25][C:24]([NH2:27])=[CH:23][CH:22]=1)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

6

Reactant 3

HCID 962WaterHCID 25517Ammonium ChlorideHCID 18552237HCID 18552237, compound

Product 1

HCID 18552227HCID 18552227, compoundYield 95.3%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

Ammonium chloride (152.9 g, 2.858 mol), 1 (225.0 g, 0.572 mol), water (2.8 L), methanol (3.8 L) were combined and mechanically stirred at 50° C., then powdered iron (95.9 g, 1.715 mol) was added portionwise over ten minutes. The suspension was vigorously stirred at reflux for 2.5 hours, then hot filtered through a celite pad. The pad was rinsed with water (3×700 mL) and CH2Cl2 (5×700 mL). The aqueous layer was extracted with CH2Cl2 (3×1 L), then concentrated to remove methanol and again extracted with CH2Cl2 (3×500 ml). The combined organics were washed with water (2×3 L), dried (Na2SO4), filtered, and spin-evaporated to give 198.1 g (95.3% yield) of 2 as a pale yellow solid. TLC (7:1 hexanes/EtOAc) indicated a single spot. This lot was combined with that of a 100 mmol run to give a total of 231 g of 2 (94.3% yield) which was suitable for further transformation.

Workup

  1. stirringThe suspension was vigorously stirred
  2. temperatureat reflux for 2.5 hours
  3. filtrationhot filtered through a celite pad
  4. washThe pad was rinsed with water (3×700 mL) and CH2Cl2 (5×700 mL)
  5. extractionThe aqueous layer was extracted with CH2Cl2 (3×1 L)
  6. concentrationconcentrated
  7. customto remove methanol
  8. extractionagain extracted with CH2Cl2 (3×500 ml)
  9. washThe combined organics were washed with water (2×3 L)
  10. dry with materialdried (Na2SO4)
  11. filtrationfiltered
  12. customspin-evaporated

Sources & evidence

ORD record
ord-7fc0acc8f4cf4e1b8108989e817af271
Source dataset
uspto-grants-2002_12
Patent number
US06495125B2

Reaction notes

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