Hexane → 2-(4-chloro-2-fluorophenyl)-5,6-dihydro-1H-imidazo[5,1-c][1,4]thiazine-1,3(2H)-dione

HRID 27007

Reaction equation

HRID 27007 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]=[C:9]=[O:10])=[C:4]([F:11])[CH:3]=1.[C:12]([C:17]1[CH2:18][S:19][CH2:20][CH2:21][N:22]=1)(OCC)=[O:13].CCCCCC>CCOCC.C(N(CC)CC)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12](=[O:13])[C:17]3=[CH:18][S:19][CH2:20][CH2:21][N:22]3[C:9]2=[O:10])=[C:4]([F:11])[CH:3]=1

Participants

6

Reactant 3

HCID 8058HexaneHCID 45582034-Chloro-2-fluorophenyl isocyanateHCID 213030583-Carbethoxy-5,6-dihydro-1,4-thiazine

Product 1

HCID 233433902-(4-chloro-2-fluorophenyl)-5,6-dihydro-1H-imidazo[5,1-c][1,4]thiazine-1,3(2H)-dioneYield 66.8%

Reagents, catalysts & solvents 2

HCID 8471TriethylamineCatalystHCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 8.6 g of 4-chloro-2-fluorophenylisocyanate in 20 ml of anhydrous ether was added dropwise to a mixture of 9.8 g of crude 3-carbethoxy-5,6-dihydro-1,4-thiazine and 10 drops of triethylamine in 20 ml of ether. After the addition, 30 ml of hexane was added dropwise in 20 min. The solution was stirred at room temperature for 3 hrs. The solution was concentrated in vacuo to remove solvent. The resulting oil was crystallized from ether to give 10 g of 2-(4-chloro-2-fluorophenyl)-5,6-dihydro-1H-imidazo[5,1-c][1,4]thiazine-1,3(2H)-dione, m.p. 117.5°-120.5° C.

Workup

  1. additionwas added dropwise in 20 min
  2. concentrationThe solution was concentrated in vacuo
  3. customto remove solvent
  4. customThe resulting oil was crystallized from ether

Sources & evidence

ORD record
ord-717bfbb6b90c4d1aae73fb1d40032188
Source dataset
uspto-grants-1980_09
Patent number
US04220465

Linked notes

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