2-Thiocresol → HCID 67550092, compound

HRID 1791404Notes

Reaction equation

HRID 1791404 reaction equation
ClN1C(=O)CCC1=O.[CH3:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[SH:16].[CH2:17]([O:19][C:20]([C:22]1[NH:23][C:24]2[C:29]([CH:30]=1)=[CH:28][C:27]([O:31][CH3:32])=[C:26]([O:33][CH3:34])[CH:25]=2)=[O:21])[CH3:18]>ClCCl>[CH2:17]([O:19][C:20]([C:22]1[NH:23][C:24]2[C:29]([C:30]=1[S:16][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[CH3:9])=[CH:28][C:27]([O:31][CH3:32])=[C:26]([O:33][CH3:34])[CH:25]=2)=[O:21])[CH3:18]

Participants

5

Reactant 3

HCID 87122-ThiocresolHCID 31398ChlorosuccinimideHCID 85385Ethyl 5,6-dimethoxy-1H-indole-2-carboxylate

Product 1

HCID 67550092HCID 67550092, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a −78° C. solution of dichloromethane (30mL) and N-chlorosuccinimide was added 2-methyl benzenethiol (0.709 mL, 6.01 mmol) dropwise. The reaction was allowed to warm 0° C. and then stirred for 30 minutes. 5,6-dimethoxy-1H-indole-2-carboxylic acid ethyl ester (Lancaster Synthesis Inc., Windham, N.H.) (1.5 g, 6.01 mmol) was added drop wise in dichloromethane (15 mL). The reaction was allowed to warm to room temperature and stirred overnight. The reaction was concentrated under reduced pressure. Methanol (5 mL) was added to the residue and a solid formed. The solid was collected, washed with diethyl ether (20 mL) and air dried to yield a beige solid (1.46 g, 66%). MS: M+−1=370.2 Da.

Workup

  1. temperatureto warm to room temperature
  2. stirringstirred overnight
  3. concentrationThe reaction was concentrated under reduced pressure
  4. additionMethanol (5 mL) was added to the residue
  5. customa solid formed
  6. customThe solid was collected
  7. washwashed with diethyl ether (20 mL) and air
  8. customdried

Sources & evidence

ORD record
ord-5e7f36c0f126469e86546f58399ac2d6
Source dataset
uspto-grants-2006_07
Patent number
US07074814B2

Reaction notes

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