Phosgene → 2-Isocyanato-5-thiomorpholin-4-yl-4-trifluoromethyl-benzoic acid methyl ester

HRID 2069271Notes

Reaction equation

HRID 2069271 reaction equation
[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[C:8]([N:10]2[CH2:15][CH2:14][S:13][CH2:12][CH2:11]2)[C:7]([C:16]([F:19])([F:18])[F:17])=[CH:6][C:5]=1[NH2:20].[C:22](Cl)(Cl)=[O:23]>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[C:8]([N:10]2[CH2:15][CH2:14][S:13][CH2:12][CH2:11]2)[C:7]([C:16]([F:17])([F:18])[F:19])=[CH:6][C:5]=1[N:20]=[C:22]=[O:23]

Participants

4

Reactant 2

HCID 6371Phosgene3×HCID 589645242-Amino-5-thiomorpholin-4-yl-4-trifluoromethyl-benzoic acid methyl ester

Product 1

HCID 589644872-Isocyanato-5-thiomorpholin-4-yl-4-trifluoromethyl-benzoic acid methyl esterYield 100%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a suspension of 100 mg (0.312 mmol) of 2-amino-5-thiomorpholin-4-yl-4-trifluoromethyl-benzoic acid methyl ester in 2 ml of dry toluene 1.5 ml of a 20% solution of phosgene in toluene are added at 0° C. After warming to room temperature, a stream of phosgene is introduced into the suspension and simultaneously heating is started. At reflux, the stream of phosgene is maintained for two hours, then replaced by a stream of argon for an additional hour. The toluene is distilled off leaving 126 mg (>100%) of 2-isocyanato-5-thiomorpholin-4-yl-4-trifluoromethyl-benzoic acid methyl ester as a brown solid, sufficiently pure for the next step. 1H-NMR (CDCl3, 360 MHz): 2.75-2.80 (m, 2H); 3.15-3.20 (m, 2H); 4.00 (s, 3H); 7.40 (s, 1H); 7.95 (s, 1H).

Workup

  1. additionare added at 0° C
  2. temperaturesimultaneously heating
  3. temperatureAt reflux
  4. waitreplaced by a stream of argon for an additional hour
  5. distillationThe toluene is distilled off

Sources & evidence

ORD record
ord-bf1201c3205c4e5ea8e60e27697237f2
Source dataset
uspto-grants-2012_10
Patent number
US08299085B2

Reaction notes

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