Water → HCID 90418121, compound

HRID 2177228Notes

Reaction equation

HRID 2177228 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:13]([CH2:14]O)=[C:12]([C:16]([CH3:18])=[CH2:17])[S:11][N:10]=2)=[CH:5][CH:4]=1)[CH3:2].CS([Cl:23])(=O)=O.C(N(CC)CC)C.O>ClCCl>[Cl:23][CH2:14][C:13]1[C:9]([C:6]2[CH:7]=[CH:8][C:3]([CH2:1][CH3:2])=[CH:4][CH:5]=2)=[N:10][S:11][C:12]=1[C:16]([CH3:18])=[CH2:17]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 90418620HCID 90418620, compound

Product 1

HCID 90418121HCID 90418121, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

Into a 50-mL round-bottom flask, was placed a solution of [3-(4-ethylphenyl)-5-(prop-1-en-2-yl)-1,2-thiazol-4-yl]methanol (305.3 mg, 1.18 mmol, 1.00 equiv) in dichloromethane (15 mL), MsCl (268.8 mg, 2.00 equiv), triethylamine (297.6 mg, 2.94 mmol, 2.50 equiv). The resulting solution was stirred for 40 min at 25° C. 10.0 mL water was added to the mixture. The organic phase was separated and washed by 10.0 mL brine, dried over anhydrous sodium sulfate. The resulting mixture was concentrated under vacuum and residue used in next step directly without further purification. Mass spectrum (ESI, m/z): Calcd. for C15H16ClNS, 278.8 (M+H). found 278.8.

Workup

  1. customInto a 50-mL round-bottom flask, was placed
  2. customThe organic phase was separated
  3. washwashed by 10.0 mL brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationThe resulting mixture was concentrated under vacuum and residue
  6. customused in next step directly without further purification

Sources & evidence

ORD record
ord-1b396fb13e064c819ac75b868d5c6ed8
Source dataset
uspto-grants-2015_06
Patent number
US09067898B1

Reaction notes

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