Triethylamine → HCID 10866837, compound

HRID 1420560Notes

Reaction equation

HRID 1420560 reaction equation
O[CH2:2][C:3]1[N:4]([CH3:11])[C:5]([N+:8]([O-:10])=[O:9])=[CH:6][CH:7]=1.CS([Cl:16])(=O)=O.CCN(CC)CC>C(Cl)Cl>[CH3:11][N:4]1[C:5]([N+:8]([O-:10])=[O:9])=[CH:6][CH:7]=[C:3]1[CH2:2][Cl:16]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 10749418HCID 10749418, compound

Product 1

HCID 10866837HCID 10866837, compoundYield 89.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A stirred solution of the above alcohol (43) (0.13 g, 0.83 mmol) in dry CH2Cl2 (5 mL) at 0° C. was treated with methanesulfonyl chloride (0.36 mL. 1.25 mmol), followed by Et3N (0.50 mL). After stirring at 0° C. for 15 min, the mixture was evaporated to dryness under reduced pressure at room temperature, and the resulting brown solid was partitioned between water and EtOAc. Workup of the organic layer gave a crude product which was was chromatographed on silica gel. Elution with CH2Cl2 /petroleum ether (1:1) gave 1-methyl-2-chloromethyl-5-nitropyrrole (44) (0.13 g, 88%), mp (EtOAc/petroleum ether) 82.5-83.5° C. 1H NMR (CDCl3) δ 7.16 (d, J=4.4 Hz, 1 H, H-4), 6.26 (d, J=4.4 Hz, 1 H, H-3), 4.60 (s, 2 H, CH2Cl), 4.02 (s, 3 H, CH3). Anal. Calculated for C6H7ClN2O2 : C, 41.3; H, 4.0; N, 16.0. Found: C, 41.4; H, 4.0; N, 15.9%.

Workup

  1. customthe mixture was evaporated to dryness under reduced pressure at room temperature
  2. customthe resulting brown solid was partitioned between water and EtOAc
  3. customWorkup of the organic layer gave a crude product which
  4. customwas was chromatographed on silica gel
  5. washElution with CH2Cl2 /petroleum ether (1:1)

Sources & evidence

ORD record
ord-3f6e3ef82db44ebc9d8fd6e0c3306e76
Source dataset
uspto-grants-2000_06
Patent number
US06071908

Reaction notes

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