Water → HCID 19966016, compound

HRID 977814Notes

Reaction equation

HRID 977814 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([S:13][CH3:14])[C:8]=1[NH:15][C:16](=[O:32])[CH2:17][CH:18]1[C:31]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[O:25][C:24]2[C:19]1=[CH:20][CH:21]=[CH:22][CH:23]=2.[CH3:33][S:34](Cl)(=[O:36])=[O:35].C(N(CC)CC)C.O>C(Cl)Cl>[S:34]([O:1][CH2:2][CH2:3][CH2:4][O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([S:13][CH3:14])[C:8]=1[NH:15][C:16](=[O:32])[CH2:17][CH:18]1[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:24]=2[O:25][C:26]2[C:31]1=[CH:30][CH:29]=[CH:28][CH:27]=2)([CH3:33])(=[O:36])=[O:35]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 19966234HCID 19966234, compound

Product 1

HCID 19966016HCID 19966016, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

212 mg (0.48 mmol) of N-[2-(3-hydroxypropoxy)methyl-6-methylthiophenyl]-2-(9H-xanthen-9-yl)acetamide (prepared as described in Preparation 4) were suspended in 15 ml of methylene chloride. The suspension was cooled on an ice bath, and then 102 mg (0.89 mmol) of methanesulfonyl chloride were added, followed by 94 mg (0.90 mmol) of triethylamine. The temperature of the reaction mixture was allowed to rise to room temperature, after which the mixture was stirred for an additional 1 hour. At the end of this time, the reaction was stopped by the addition of water. The mixture was then diluted with methylene chloride, after which the organic layer was washed with dilute aqueous hydrochloric acid and then with water. The solvent was then removed by distillation under reduced pressure, to obtain 251 mg (a quantitative yield) of the title compound as crystals. These crystals were used for the next step without purification.

Workup

  1. temperatureThe suspension was cooled on an ice bath
  2. customto rise to room temperature
  3. washafter which the organic layer was washed with dilute aqueous hydrochloric acid
  4. customThe solvent was then removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-482b414fc9aa45b1a65f6f3b45ad1a64
Source dataset
uspto-grants-1997_03
Patent number
US05614550

Reaction notes

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