Dimethyl Sulfide → HCID 12510286, compound

HRID 66098Notes

Reaction equation

HRID 66098 reaction equation
ClCl.[CH3:3][S:4][CH3:5].[C:6]12([O:16][C:17]3[CH:23]=[CH:22][C:20]([NH2:21])=[CH:19][CH:18]=3)[CH2:15][CH:10]3[CH2:11][CH:12]([CH2:14][CH:8]([CH2:9]3)[CH2:7]1)[CH2:13]2.C(N(CC)CC)C>C(Cl)Cl>[C:6]12([O:16][C:17]3[CH:18]=[CH:19][C:20]([NH2:21])=[C:22]([CH2:3][S:4][CH3:5])[CH:23]=3)[CH2:13][CH:12]3[CH2:11][CH:10]([CH2:9][CH:8]([CH2:14]3)[CH2:7]1)[CH2:15]2

Participants

6

Reactant 4

HCID 1068Dimethyl SulfideHCID 8471TriethylamineHCID 24526ChlorineHCID 72894774-(1-Adamantyloxy)aniline

Product 1

HCID 12510286HCID 12510286, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To 6.2 g. (0.088 mole) of chlorine in 240 ml. of CH2Cl2 in one-liter 3-neck flask cooled to -70° to -73° was added dropwise with stirring a cold (~ -70° ) solution of 5.7 g. (0.092 mole) of dimethyl sulfide in 20 ml. of CH2Cl2. The solution was stirred for several minutes, and then a solution of 21.4 g. (0.088 mole) of 4-(1-adamantyloxy)-aniline and 8.9 g. (0.088 mole) of triethylamine in 400 ml. of CH2Cl2 cooled either to -70° or to -40° to -50° was added dropwise rapidly. Then the mixture was either stirred at -70° and gradually allowed to warm to room temperature during four hours and then cooled again to -65° or it was stirred at -70° for 2 hours followed in either case by the addition of 51.8 g. of 25% sodium methoxide in methanol solution, removal of the cold bath, and stirring at room temperature for 12 to 18 hours.

Workup

  1. additionwas added dropwise
  2. stirringThe solution was stirred for several minutes
  3. additionwas added dropwise rapidly
  4. stirringThen the mixture was either stirred at -70°
  5. temperaturecooled again to -65°
  6. stirringit was stirred at -70° for 2 hours
  7. additionfollowed in either case by the addition of 51.8 g
  8. customof 25% sodium methoxide in methanol solution, removal of the cold bath
  9. stirringstirring at room temperature for 12 to 18 hours

Sources & evidence

ORD record
ord-5cdceafc1414433a820a269f6ec37af9
Source dataset
uspto-grants-1978_12
Patent number
US04130561

Reaction notes

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