Hydrochloric Acid → HCID 20202897, compound

HRID 978442Notes

Reaction equation

HRID 978442 reaction equation
C(=O)([O-])[O-].[Ca+2].[NH2:6][C:7]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][C:8]=1[C:9]([O:11][CH2:12][CH3:13])=[O:10].Cl.[C:20](Cl)(Cl)=[S:21]>O.ClC(Cl)Cl>[OH:18][C:15]1[CH:16]=[CH:17][C:7]([N:6]=[C:20]=[S:21])=[C:8]([CH:14]=1)[C:9]([O:11][CH2:12][CH3:13])=[O:10]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 10040ThiophosgeneHCID 10112Calcium CarbonateHCID 20202894HCID 20202894, compound

Product 1

HCID 20202897HCID 20202897, compoundYield 67.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent3×HCID 6212ChloroformSolvent2×

Conditions

Temperature
10 °C

Procedure

To a stirred mixture of 5 parts of calcium carbonate, 18.75 parts of trichloromethane and 12.5 parts of water were added 3.6 parts of ethyl 2-amino-5-hydroxybenzoate. 3 Parts of concentrate hydrochloric acid and 10 parts of water were added and the whole was stirred for 15 minutes under nitrogen atmosphere. After cooling in an ice bath at 10° C., 2.6 parts of carbonothioic dichloride were added dropwise, during a period of 20 minutes, at 10°-15° C. The whole was allowed to reach room temperature and stirring was continued for 2 hours. 300 Parts of trichloromethane and 200 parts of water were added. The organic layer was separated, washed with a hydrochloric acid solution 1N and with a sodium hydrogen carbonate solution 10%, dried, filtered and evaporated. The residue was crystallized from 45 parts of benzene. The product was filtered off and dried, yielding 3.0 parts (67.1%) of ethyl 5-hydroxy-2-isothiocyanatobenzoate (18).

Workup

  1. customto reach room temperature
  2. stirringstirring
  3. waitwas continued for 2 hours
  4. customThe organic layer was separated
  5. washwashed with a hydrochloric acid solution 1N and with a sodium hydrogen carbonate solution 10%
  6. customdried
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was crystallized from 45 parts of benzene
  10. filtrationThe product was filtered off
  11. customdried

Sources & evidence

ORD record
ord-d78d7e55591f4c4992e253aef50502c9
Source dataset
uspto-grants-1987_05
Patent number
US04665075

Reaction notes

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