Trichloroacetyl chloride → HCID 89726899, compound

HRID 926354Notes

Reaction equation

HRID 926354 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[CH:8][N:9]2[CH2:14][CH2:13][S:12][CH2:11][C:10]=12)=[O:5])[CH3:2].[Cl:15][C:16]([Cl:21])([Cl:20])[C:17](Cl)=[O:18]>ClCCl>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[C:8]([C:17](=[O:18])[C:16]([Cl:21])([Cl:20])[Cl:15])[N:9]2[CH2:14][CH2:13][S:12][CH2:11][C:10]=12)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 6420Trichloroacetyl chloride2×HCID 89726514HCID 89726514, compound

Product 1

HCID 89726899HCID 89726899, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3,4-dihydro-1H-pyrrolo[2,1-c][1,4]thiazine-8-carboxylic acid ethyl ester (Comp. No. 2c) (0.5 g, 2.37 mmol) in anhydrous dichloromethane (1.7 ml) was added trichloro-acetyl chloride (1.08 g, 5.9 mmol). The resulting mixture was stirred overnight at room temperature, after which a second portion of trichloro-acetyl chloride (0.43 g, 2.37 mmol) was added. The resulting mixture was stirred for 4 h, and then evaporated to dryness. The crude product was purified by silica gel chromatography (eluting with 5 to 50% ethyl acetate in heptane) to give 0.592 g of 6-(2,2,2-Trichloro-acetyl)-3,4-dihydro-1H-pyrrolo[2,1-c][1,4]thiazine-8-carboxylic acid ethyl ester. LC/MS (method 4): Rt=1.41 min; m/z=356.09 (M+H+).

Workup

  1. stirringThe resulting mixture was stirred for 4 h
  2. customevaporated to dryness
  3. customThe crude product was purified by silica gel chromatography (eluting with 5 to 50% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-be039add46e04409809ae783e79f12d0
Source dataset
uspto-grants-2016_03
Patent number
US09284333B2

Reaction notes

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