Triethylamine → 6-Benzyloxy-4-(methylsulfonyl)amino-2,2-dimethylchroman

HRID 567057Notes

Reaction equation

HRID 567057 reaction equation
[NH2:1][CH:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH:10]=2)[O:5][C:4]([CH3:21])([CH3:20])[CH2:3]1.C(N(CC)CC)C.[CH3:29][S:30](Cl)(=[O:32])=[O:31]>C1COCC1>[CH2:13]([O:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[O:5][C:4]([CH3:21])([CH3:20])[CH2:3][CH:2]2[NH:1][S:30]([CH3:29])(=[O:32])=[O:31])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 212645054-Amino-6-benzyloxy-2,2-dimethylchroman

Product 1

HCID 212645206-Benzyloxy-4-(methylsulfonyl)amino-2,2-dimethylchroman

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4.0 g (14 mmol) of 4-amino-6-benzyloxy-2,2-dimethylchroman were treated with 4.2 ml (30 mmol) of triethylamine at RT in 80 ml of THF and the mixture was stirred for 30 min, then treated with 1.95 g (1.3 ml, 17 mmol) of methanesulfonyl chloride, the temperature rising to 40° C. The mixture was then heated to reflux for 2 h, allowed to stand overnight at RT, concentrated in vac. and the residue was treated with water; 4.9 g of product, m.p. 162-165° C.

Workup

  1. customrising to 40° C
  2. temperatureThe mixture was then heated
  3. temperatureto reflux for 2 h
  4. waitto stand overnight at RT
  5. concentrationconcentrated in vac
  6. additionand the residue was treated with water

Sources & evidence

ORD record
ord-497e8fb376f0492cb14d08f599fa03d4
Source dataset
uspto-grants-2001_01
Patent number
US06177449B1

Reaction notes

Loading…