Acetic Anhydride → 1-Nitro-1-(1,3-thiazinan-2-ylidene)propan-2-one

HRID 1657698Notes

Reaction equation

HRID 1657698 reaction equation
[N+:1]([CH:4]=[C:5]1[NH:10][CH2:9][CH2:8][CH2:7][S:6]1)([O-:3])=[O:2].[C:11](OC(=O)C)(=[O:13])[CH3:12]>>[N+:1]([C:4](=[C:5]1[NH:10][CH2:9][CH2:8][CH2:7][S:6]1)[C:11](=[O:13])[CH3:12])([O-:3])=[O:2]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 428532-nitromethylenetetrahydro-2H-1,3-thiazine

Product 1

HCID 714007471-Nitro-1-(1,3-thiazinan-2-ylidene)propan-2-one

Procedure

4.0 g of 2b was added in portions to 50 ml of acetic anhydride at 25°. The solution was heated at 95°-105° for 2 hours. Excess acetic anhydride was removed under reduced pressure to leave 5.0 g of a slightly gummy brown solid which was crystallized from ethyl acetate (after treatment with charcoal) to give 2 as a yellow-brown solid, m.p.: 110°-113°.

Workup

  1. temperatureThe solution was heated at 95°-105° for 2 hours
  2. customExcess acetic anhydride was removed under reduced pressure
  3. customto leave 5.0 g of a slightly gummy brown solid which
  4. customwas crystallized from ethyl acetate (after treatment with charcoal)

Sources & evidence

ORD record
ord-2462e575417a4bc48788d29671add83e
Source dataset
uspto-grants-1976_06
Patent number
US03962225

Reaction notes

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