Triethylamine → HCID 70201478, compound

HRID 342469Notes

Reaction equation

HRID 342469 reaction equation
[NH2:1][C:2]1[C:3]([Cl:25])=[C:4]([C:21]([Cl:24])=[CH:22][CH:23]=1)[C:5]([NH:7][C:8]1[C:16]2[O:15][C:14]3[CH2:17][CH2:18][CH2:19][CH2:20][C:13]=3[C:12]=2[CH:11]=[CH:10][CH:9]=1)=[O:6].[CH3:26][S:27](Cl)(=[O:29])=[O:28].C(N(CC)CC)C>ClCCl>[Cl:25][C:3]1[C:2]([N:1]([S:27]([CH3:26])(=[O:29])=[O:28])[S:27]([CH3:26])(=[O:29])=[O:28])=[CH:23][CH:22]=[C:21]([Cl:24])[C:4]=1[C:5]([NH:7][C:8]1[C:16]2[O:15][C:14]3[CH2:17][CH2:18][CH2:19][CH2:20][C:13]=3[C:12]=2[CH:11]=[CH:10][CH:9]=1)=[O:6]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 54054228HCID 54054228, compound

Product 1

HCID 70201478HCID 70201478, compoundYield 61.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 6-(3-amino-2,6-dichlorobenzoylamino)-1,2,3,4-tetrahydrodibenzofuran (100 mg), methanesulfonyl chloride (120 mg) and triethylamine (162 mg) in dichloromethane (3 ml) was stirred at ambient temperature for 2 hours. The reaction mixture was diluted with dichloromethane and washed with 1N-hydrochloric acid, aqueous saturated sodium bicarbonate and brine. The solution was dried over sodium sulfate and concentrated in vacuo. The residual oil was crystallized from ethanol to give 6-[2,6-dichloro-3-bis(methanesulfonyl)aminobenzoyl-amino]-1,2,3,4-tetrahydrodibenzofuran (87 mg).

Workup

  1. washwashed with 1N-hydrochloric acid, aqueous saturated sodium bicarbonate and brine
  2. dry with materialThe solution was dried over sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe residual oil was crystallized from ethanol

Sources & evidence

ORD record
ord-3c074af8ec794170a428ac4ed7a75516
Source dataset
uspto-grants-1999_01
Patent number
US05858995

Reaction notes

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