Hydrochloric Acid → HCID 69885139, compound

HRID 47748Notes

Reaction equation

HRID 47748 reaction equation
C([NH:5][C:6]([NH:8][C@H:9]([CH2:12][CH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1)[CH2:10]O)=[S:7])(C)(C)C.[ClH:19]>>[ClH:19].[CH:13]1([CH2:12][C@@H:9]2[CH2:10][S:7][C:6]([NH2:5])=[N:8]2)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 86584435HCID 86584435, compound

Product 1

HCID 69885139HCID 69885139, compound

Conditions

Temperature
100 °C

Procedure

The process is performed as in Example 1, starting with 2.9 g of N-(tert-butyl)-N′-[(1R)-1-cyclohexylmethyl-2-hydroxyethyl]thiourea in 28 cm3 of aqueous 6N hydrochloric acid by heating at a temperature in the region of 100° C. for 2 h 15 min. By means of an identical work-up, a solid is obtained which is purified by dissolution in 15 cm3 of water and extraction with 10 cm3 of dichloromethane. The aqueous phase is made alkaline by addition of 10 cm3 of 1N sodium hydroxide and is extracted with twice 15 cm3 of ethyl acetate. The combined organic extracts are concentrated under reduced pressure (5 kPa) at a temperature in the region of 40° C. The resulting paste is taken up in twice 20 cm3 of diethyl ether. The solid is filtered off and dried in an oven under reduced pressure (10 Pa) at a temperature in the region of 60° C. 0.4 g of (+)-(4R)-4-cyclohexylmethyl-4,5-dihydro-1,3-thiazol-2-ylamine hydrochloride is obtained in the form of a white solid melting at 169° C. (αD20=+31.8±0.9 at a concentration of 0.5% in methanol).

Workup

  1. customBy means of an identical work-up, a solid is obtained which
  2. customis purified by dissolution in 15 cm3 of water
  3. extractionextraction with 10 cm3 of dichloromethane
  4. additionby addition of 10 cm3 of 1N sodium hydroxide
  5. extractionis extracted with twice 15 cm3 of ethyl acetate
  6. concentrationThe combined organic extracts are concentrated under reduced pressure (5 kPa) at a temperature in the region of 40° C
  7. filtrationThe solid is filtered off
  8. customdried in an oven under reduced pressure (10 Pa) at a temperature in the region of 60° C

Sources & evidence

ORD record
ord-556b44f1836845979d83e8abb1311306
Source dataset
uspto-grants-2004_03
Patent number
US06699895B2

Reaction notes

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