Triethylamine → HCID 53727159, compound

HRID 1248005Notes

Reaction equation

HRID 1248005 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(N(CC)CC)C.Cl[C:19]([O:21][CH2:22][CH2:23][Br:24])=[O:20]>ClCCl>[Br:24][CH2:23][CH2:22][O:21][C:19]([N:10]1[CH2:9][CH2:8][CH2:7][S:6][C:5]1=[CH:4][N+:1]([O-:3])=[O:2])=[O:20]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 428532-nitromethylenetetrahydro-2H-1,3-thiazineHCID 785282-Bromoethyl chloroformate

Product 1

HCID 53727159HCID 53727159, compoundYield 79.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a mixture of 12.8 g 2-nitromethylene-tetrahydro-2H-1,3-thiazine, 21 ml triethylamine and 120 ml dichloro methane was added dropwise over 75 minutes, at -30° C. under nitrogen, a solution of 18 g 2-bromoethyl chloroformate in 100 ml dichloro methane. The reaction mixture was allowed to warm to 0° C., over 30 minutes, with stirring, and then washed with 2% hydrochloric acid. The organic phase was separated off and dried (MgSO4), and the solvent was evaporated off. The solid material (27.2 g) was purified on a silica gel column using a 199:1 mixture (vol/vol) of dichloro methane and methanol, to yield 19.7 g of crystals, having a melting point of 79°-81° C.

Workup

  1. additionwas added dropwise over 75 minutes, at -30° C. under nitrogen
  2. washwashed with 2% hydrochloric acid
  3. customThe organic phase was separated off
  4. dry with materialdried (MgSO4)
  5. customthe solvent was evaporated off
  6. customThe solid material (27.2 g) was purified on a silica gel column

Sources & evidence

ORD record
ord-aad49201558e4a00ac9f68e34dd3aa45
Source dataset
uspto-grants-1985_06
Patent number
US04521536

Reaction notes

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