Sodium Bicarbonate → HCID 67275726, compound

HRID 1698497Notes

Reaction equation

HRID 1698497 reaction equation
[NH2:1][CH:2]([C:7]1[CH:12]=[CH:11][C:10]([S:13][CH2:14][CH:15]2[CH2:17][CH2:16]2)=[CH:9][CH:8]=1)[C:3]([CH3:6])([OH:5])[CH3:4].[Cl:18][C:19]1[C:27]([C:28]([F:31])([F:30])[F:29])=[CH:26][CH:25]=[CH:24][C:20]=1[C:21](Cl)=[O:22].C(=O)(O)[O-].[Na+]>ClCCl>[Cl:18][C:19]1[C:27]([C:28]([F:29])([F:30])[F:31])=[CH:26][CH:25]=[CH:24][C:20]=1[C:21]([NH:1][CH:2]([C:7]1[CH:8]=[CH:9][C:10]([S:13][CH2:14][CH:15]2[CH2:16][CH2:17]2)=[CH:11][CH:12]=1)[C:3]([OH:5])([CH3:6])[CH3:4])=[O:22]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 38276332-Chloro-3-(trifluoromethyl)benzoyl chlorideHCID 67275555HCID 67275555, compound

Product 1

HCID 67275726HCID 67275726, compoundYield 69.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-Amino-1-(4-[(cyclopropylmethyl)thio]phenyl)-2-methylpropan-2-ol (150 mg) and 2-chloro-3-(trifluoromethyl)benzoyl chloride (300 mg) in dichloromethane (2 mL) were treated with saturated sodium bicarbonate solution (2 mL) and stirred vigorously for 16 h. The organic phase was dried (MgSO4), concentrated and the residue purified by chromatography on silica (eluting with iso-hexane on a gradient of ethyl acetate) to give the title compound as a foam (189 mg). 1H NMR (500 MHz, CDCl3): δ 7.76 (1H, d, J=7.8 Hz), 7.64 (1H, d, J=7.6 Hz), 7.41 (1H, t, J=7.8 Hz), 7.34 (2H, d, J=8.2 Hz), 7.28 (2H, d, J=8.2 Hz), 7.05 (1H, br d, J=8.5 Hz), 4.98 (1H, d, J=8.5 Hz), 2.87 (2H, d, J=7.0 Hz), 1.45 (3H, s), 1.10 (3H, s), 1.09-1.04 (1H, m), 0.59 (2H, q, J=5:1 Hz), 0.26 (2H, q, J=5.1 Hz); m/z 457, 459.

Workup

  1. dry with materialThe organic phase was dried (MgSO4)
  2. concentrationconcentrated
  3. customthe residue purified by chromatography on silica (
  4. washeluting with iso-hexane on a gradient of ethyl acetate)

Sources & evidence

ORD record
ord-6ad365e270ca45b7997a630fbd1f89fc
Source dataset
uspto-grants-2012_04
Patent number
US08163956B2

Reaction notes

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