Phenylacetyl chloride → 3-(Phenylacetyl)-2-nitromethylene-tetrahydro-2H-1,3-thiazine

HRID 371081Notes

Reaction equation

HRID 371081 reaction equation
[C:1]1([CH2:7][C:8](Cl)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[N+:18]([CH:21]=[C:22]1[NH:27][CH2:26][CH2:25][CH2:24][S:23]1)([O-:20])=[O:19]>ClCCl>[C:1]1([CH2:7][C:8]([N:27]2[CH2:26][CH2:25][CH2:24][S:23][C:22]2=[CH:21][N+:18]([O-:20])=[O:19])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 7679Phenylacetyl chlorideHCID 8471TriethylamineHCID 428532-nitromethylenetetrahydro-2H-1,3-thiazine

Product 1

HCID 538965883-(Phenylacetyl)-2-nitromethylene-tetrahydro-2H-1,3-thiazine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of phenylacetyl chloride (4.8 g) in dry dichloromethane (30 ml) at -20° C. was added triethylamine (5.2 ml) over a period of 20 minutes, followed by 2-(nitromethylene)-tetrahydro-2H-1,3-thiazine (3.2 g) in dry dichloromethane (30 ml) over a period of 20 minutes. The reaction mixture was allowed to warm to ambient temperature with stirring over a period of 30 minutes and was then worked up in a similar manner to that described in Example 1 to yield the required product as a white crystalline solid m.p. 121°-122° C.

Sources & evidence

ORD record
ord-a49b3e79590b499e923373739244dbc7
Source dataset
uspto-grants-1985_07
Patent number
US04529726

Reaction notes

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